IL128693A - Process for synthesizing aromatic acyl halides by the grignard reaction with phosgene - Google Patents

Process for synthesizing aromatic acyl halides by the grignard reaction with phosgene

Info

Publication number: IL128693A
Authority: IL; Israel
Prior art keywords: alkyl; formula; aryl; compound; heteroaryl
Prior art date: 1998-03-09

Application number

IL12869399A

Other languages

English (en)

Other versions

IL128693A0 (en

Original Assignee

Rohm & Haas

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-03-09

Filing date

1999-02-24

Publication date

2002-02-10

1999-02-24 Application filed by Rohm & Haas filed Critical Rohm & Haas

2000-01-31 Publication of IL128693A0 publication Critical patent/IL128693A0/xx

2002-02-10 Publication of IL128693A publication Critical patent/IL128693A/en

Links

238000000034 method Methods 0.000 title claims abstract description 38
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 title claims abstract description 26
-1 aromatic acyl halides Chemical class 0.000 title abstract description 28
238000003747 Grignard reaction Methods 0.000 title description 13
230000002194 synthesizing effect Effects 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 127
150000001875 compounds Chemical class 0.000 claims abstract description 93
125000003118 aryl group Chemical group 0.000 claims abstract description 82
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 59
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
239000003513 alkali Substances 0.000 claims abstract description 26
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 19
239000003054 catalyst Substances 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 18
239000010949 copper Substances 0.000 claims abstract description 14
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052802 copper Inorganic materials 0.000 claims abstract description 13
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 11
125000001246 bromo group Chemical group Br* 0.000 claims abstract description 10
125000002346 iodo group Chemical group I* 0.000 claims abstract description 8
150000004703 alkoxides Chemical class 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims description 27
230000015572 biosynthetic process Effects 0.000 claims description 13
150000004795 grignard reagents Chemical class 0.000 claims description 9
239000007818 Grignard reagent Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
238000010791 quenching Methods 0.000 claims description 5
230000000171 quenching effect Effects 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
150000001263 acyl chlorides Chemical class 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000006536 (C1-C2)alkoxy group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
239000000203 mixture Substances 0.000 description 51
238000006243 chemical reaction Methods 0.000 description 45
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
229910052757 nitrogen Inorganic materials 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 0.000 description 19
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 19
238000010992 reflux Methods 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000010410 layer Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
229910002092 carbon dioxide Inorganic materials 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
239000001569 carbon dioxide Substances 0.000 description 13
238000005755 formation reaction Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
229910052749 magnesium Inorganic materials 0.000 description 10
239000011777 magnesium Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 9
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 9
238000004817 gas chromatography Methods 0.000 description 9
BXKZGIVKHPCDFO-UHFFFAOYSA-N 3-methoxy-2-methylbenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1C BXKZGIVKHPCDFO-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
150000001502 aryl halides Chemical class 0.000 description 8
238000006198 methoxylation reaction Methods 0.000 description 8
150000007524 organic acids Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
LHVJUPHCLWIPLZ-UHFFFAOYSA-N 3-acetyloxy-2-methylbenzoic acid Chemical compound CC(=O)OC1=CC=CC(C(O)=O)=C1C LHVJUPHCLWIPLZ-UHFFFAOYSA-N 0.000 description 6
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
235000010233 benzoic acid Nutrition 0.000 description 6
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
235000011089 carbon dioxide Nutrition 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
238000005191 phase separation Methods 0.000 description 6
239000002002 slurry Substances 0.000 description 6
229910021589 Copper(I) bromide Inorganic materials 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000007789 gas Substances 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
239000007787 solid Substances 0.000 description 5
DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 description 4
RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000002024 ethyl acetate extract Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000012535 impurity Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
125000006526 (C1-C2) alkyl group Chemical group 0.000 description 3
LTVRGAWOEOKGJZ-UHFFFAOYSA-N 1-chloro-3-methoxy-2-methylbenzene Chemical compound COC1=CC=CC(Cl)=C1C LTVRGAWOEOKGJZ-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
JPCISVSOTKMFPG-UHFFFAOYSA-N 3-methoxy-2-methylbenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1C JPCISVSOTKMFPG-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000001559 benzoic acids Chemical class 0.000 description 3
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000005661 deetherification reaction Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical group O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 3
239000003999 initiator Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001491 aromatic compounds Chemical group 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000002102 aryl alkyloxo group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006473 carboxylation reaction Methods 0.000 description 2
239000000969 carrier Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000010586 diagram Methods 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000004446 heteroarylalkyl group Chemical group 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
229940086542 triethylamine Drugs 0.000 description 2
MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
HXGHMCLCSPQMOR-UHFFFAOYSA-N 3-chloro-2-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC=C1C(O)=O HXGHMCLCSPQMOR-UHFFFAOYSA-N 0.000 description 1
JPKBIODDVOUHAD-UHFFFAOYSA-N 3-methoxy-2-methylbenzonitrile Chemical compound COC1=CC=CC(C#N)=C1C JPKBIODDVOUHAD-UHFFFAOYSA-N 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
150000001500 aryl chlorides Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
XDFCIPNJCBUZJN-UHFFFAOYSA-N barium(2+) Chemical compound [Ba+2] XDFCIPNJCBUZJN-UHFFFAOYSA-N 0.000 description 1
BQDSDRAVKYTTTH-UHFFFAOYSA-N barium(2+);methanolate Chemical compound [Ba+2].[O-]C.[O-]C BQDSDRAVKYTTTH-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 description 1
JHLCADGWXYCDQA-UHFFFAOYSA-N calcium;ethanolate Chemical compound [Ca+2].CC[O-].CC[O-] JHLCADGWXYCDQA-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
XAVQZBGEXVFCJI-UHFFFAOYSA-M lithium;phenoxide Chemical compound [Li+].[O-]C1=CC=CC=C1 XAVQZBGEXVFCJI-UHFFFAOYSA-M 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
KRPXAHXWPZLBKL-UHFFFAOYSA-L magnesium;diphenoxide Chemical compound [Mg+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 KRPXAHXWPZLBKL-UHFFFAOYSA-L 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
125000004436 sodium atom Chemical group 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
YTBRWVXQNMQQTK-UHFFFAOYSA-N strontium;ethanolate Chemical compound CCO[Sr]OCC YTBRWVXQNMQQTK-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
239000008096 xylene Substances 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

IL12869399A 1998-03-09 1999-02-24 Process for synthesizing aromatic acyl halides by the grignard reaction with phosgene IL128693A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7725898P	1998-03-09	1998-03-09
US09/218,571 US6124500A (en)	1998-03-09	1998-12-22	Process for synthesizing benzoic acids

Publications (2)

Publication Number	Publication Date
IL128693A0 IL128693A0 (en)	2000-01-31
IL128693A true IL128693A (en)	2002-02-10

Family

ID=26759081

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12869399A IL128693A (en)	1998-03-09	1999-02-24	Process for synthesizing aromatic acyl halides by the grignard reaction with phosgene

Country Status (10)

Country	Link
US (1)	US6124500A (de)
EP (1)	EP0941982B1 (de)
JP (3)	JP4560609B2 (de)
KR (1)	KR100603174B1 (de)
CN (1)	CN1095823C (de)
AU (1)	AU747349B2 (de)
BR (2)	BR9900974B1 (de)
DE (1)	DE69907056T2 (de)
IL (1)	IL128693A (de)
TW (1)	TWI236467B (de)

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CN102249901A (zh) *	2011-05-13	2011-11-23	山东非金属材料研究所	一种2,5-二烷氧基对苯二甲酸的制备方法
CN102211996A (zh) *	2011-05-13	2011-10-12	山东非金属材料研究所	一种2,5-二羟基对苯二甲酸的制备方法
CN103387494B (zh) *	2012-05-10	2016-08-03	上海医药工业研究院	制备2-羟基-4,5-二甲氧基苯甲酸的方法
WO2014207206A1 (en) *	2013-06-27	2014-12-31	Dpx Holdings B.V.	Preparation of grignard reagents using a fluidized bed
CN107793308A (zh) *	2016-08-31	2018-03-13	江苏万隆科技有限公司	一种2‑甲基‑3‑甲氧基苯甲酸的合成方法
CN107778167A (zh) *	2016-08-31	2018-03-09	江苏万隆科技有限公司	2‑甲基‑3‑甲氧基苯甲酸的制备方法
CN107176908A (zh) *	2017-05-12	2017-09-19	江苏科菲特生化技术股份有限公司	一种2‑甲基‑3‑甲氧基苯甲酰氯的合成方法
CN108929217B (zh) *	2017-05-26	2021-02-26	浙江天宇药业股份有限公司	一种2-甲基-5-氟苯甲酸的制备方法
CN111018693A (zh) *	2020-01-02	2020-04-17	西安正阳嘉禾化工科技有限公司	一种2-甲基-3-甲氧基苯甲酸及其制备方法
CN115894211A (zh) *	2022-11-10	2023-04-04	山东龙立恒医药有限公司	一种3-羟基-4-甲基苯甲酸的制备方法

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1998
- 1998-12-22 US US09/218,571 patent/US6124500A/en not_active Expired - Lifetime
1999
- 1999-02-22 AU AU17427/99A patent/AU747349B2/en not_active Ceased
- 1999-02-24 IL IL12869399A patent/IL128693A/en not_active IP Right Cessation
- 1999-03-02 DE DE69907056T patent/DE69907056T2/de not_active Expired - Lifetime
- 1999-03-02 EP EP99301536A patent/EP0941982B1/de not_active Expired - Lifetime
- 1999-03-08 BR BRPI9900974-9A patent/BR9900974B1/pt not_active IP Right Cessation
- 1999-03-08 BR BRPI9917810-9A patent/BR9917810B1/pt not_active IP Right Cessation
- 1999-03-09 JP JP06108699A patent/JP4560609B2/ja not_active Expired - Fee Related
- 1999-03-09 KR KR1019990007737A patent/KR100603174B1/ko not_active Expired - Fee Related
- 1999-03-09 CN CN99102914A patent/CN1095823C/zh not_active Expired - Lifetime
- 1999-03-09 TW TW088103599A patent/TWI236467B/zh not_active IP Right Cessation
2009
- 2009-09-02 JP JP2009202490A patent/JP5091929B2/ja not_active Expired - Fee Related
2012
- 2012-08-14 JP JP2012179852A patent/JP2012255014A/ja active Pending

Also Published As

Publication number	Publication date
CN1232018A (zh)	1999-10-20
EP0941982B1 (de)	2003-04-23
BR9917810B1 (pt)	2011-12-13
DE69907056D1 (de)	2003-05-28
JP5091929B2 (ja)	2012-12-05
JP2010013464A (ja)	2010-01-21
US6124500A (en)	2000-09-26
BR9900974B1 (pt)	2011-04-19
BR9900974A (pt)	2000-05-30
EP0941982A3 (de)	1999-12-08
AU747349B2 (en)	2002-05-16
KR100603174B1 (ko)	2006-07-24
DE69907056T2 (de)	2003-11-06
JP4560609B2 (ja)	2010-10-13
JP2012255014A (ja)	2012-12-27
IL128693A0 (en)	2000-01-31
CN1095823C (zh)	2002-12-11
EP0941982A2 (de)	1999-09-15
TWI236467B (en)	2005-07-21
KR19990046003A (ko)	1999-06-25
AU1742799A (en)	1999-09-23
JPH11322664A (ja)	1999-11-24

Legal Events

Date	Code	Title
2002-06-30	FF	Patent granted
2002-08-14	HP	Change in proprietorship
2002-08-14	KB	Patent renewed
2005-03-20	KB	Patent renewed
2009-07-27	KB	Patent renewed
2013-02-03	KB	Patent renewed
2017-09-28	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
JP5091929B2 (ja)	2012-12-05	安息香酸類の製造方法
US5886210A (en)	1999-03-23	Method for preparing aromatic compounds
EP0831083B1 (de)	2001-03-14	Verfahren zur Herstellung von Benzoesäure-Derivaten
GB1599623A (en)	1981-10-07	2-(2,2-dihalovinyl)-thiophenes
JP2609966B2 (ja)	1997-05-14	２−置換ベンゾ［ｂ］チオフェンおよびその中間体の製造方法
MXPA99002227A (en)	2000-12-06	Process to synthesize benzoi acids
JP2600327B2 (ja)	1997-04-16	光学活性なカルボン酸エステル類およびその製造方法
JP3118596B2 (ja)	2000-12-18	アリールジアルキルチオカルバマート、２−メルカプトベンズアルデヒドおよび２−置換ベンゾ［ｂ］チオフェンの製造方法
JP4251508B2 (ja)	2009-04-08	酸塩化物化合物の製造方法
JP4028624B2 (ja)	2007-12-26	芳香族化合物の製造方法
WO2001094289A1 (en)	2001-12-13	Process for the preparation of bromoisophthalic acid compounds
JP3545466B2 (ja)	2004-07-21	ジヒドロクロマンカルボン酸類及びその製造方法
JP2002179612A (ja)	2002-06-26	２，３−ジブロモ琥珀酸類の製造方法
US4982010A (en)	1991-01-01	Method of producing 4-biphenyl p-tolyl ether
JPH10182544A (ja)	1998-07-07	ｐ−アシルアルキルベンゼン誘導体の製造法
JP2816855B2 (ja)	1998-10-27	ピリジン―２，３―ジカルボン酸誘導体の製造方法
JP2003252831A (ja)	2003-09-10	含フッ素乳酸誘導体の製造方法
JPH0583537B2 (de)	1993-11-26
MXPA97006960A (en)	1998-11-09	Process to synthesize benzoic acids
JPS6310706B2 (de)	1988-03-08
JPH0372054B2 (de)	1991-11-15
JPH11171849A (ja)	1999-06-29	臭化ベンジル誘導体の製造法
JPH035381B2 (de)	1991-01-25
JP2002060370A (ja)	2002-02-26	ブロモイソフタル酸化合物の製造方法
JPH0477454A (ja)	1992-03-11	アセチレンジカルボン酸エステルの製造方法