DD153203A5 - Verfahren zur herstellung neuer 4-fluor-3-phenoxy-benzyl-ether - Google Patents

Verfahren zur herstellung neuer 4-fluor-3-phenoxy-benzyl-ether Download PDF

Info

Publication number: DD153203A5
Authority: DD; German Democratic Republic
Prior art keywords: fluoro; benzyl; bromo; ether; formula
Prior art date: 1979-08-22

Application number

DD223395A

Other languages

German (de)

English (en)

Inventor

Fuchs

Maurer

Priesnitz

Riebel

Klauke

Original Assignee

Bayer Ag

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.)

1979-08-22

Filing date

1980-08-19

Publication date

1981-12-30

1980-08-19 Application filed by Bayer Ag filed Critical Bayer Ag

1981-12-30 Publication of DD153203A5 publication Critical patent/DD153203A5/de

Links

DIIWCXHABNUDCX-UHFFFAOYSA-N 1-fluoro-4-[(4-fluoro-3-phenoxyphenyl)methoxymethyl]-2-phenoxybenzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1COCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 DIIWCXHABNUDCX-UHFFFAOYSA-N 0.000 title claims abstract description 5
238000004519 manufacturing process Methods 0.000 title description 5
238000000034 method Methods 0.000 claims abstract description 45
238000002360 preparation method Methods 0.000 claims abstract description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
239000003085 diluting agent Substances 0.000 claims description 17
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
229910052802 copper Inorganic materials 0.000 claims description 5
239000010949 copper Substances 0.000 claims description 5
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
RHBWFQLSCSSDBR-UHFFFAOYSA-N 2-bromo-4-[(3-bromo-4-fluorophenyl)methoxymethyl]-1-fluorobenzene Chemical compound C1=C(Br)C(F)=CC=C1COCC1=CC=C(F)C(Br)=C1 RHBWFQLSCSSDBR-UHFFFAOYSA-N 0.000 claims description 3
239000005749 Copper compound Substances 0.000 claims description 3
150000001880 copper compounds Chemical class 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
150000004707 phenolate Chemical class 0.000 claims description 3
239000000543 intermediate Substances 0.000 abstract description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
-1 3-bromo-4-fluoro-benzyl halides Chemical class 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 16
239000002904 solvent Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
HNVVROFWONXXGO-UHFFFAOYSA-N (3-bromo-4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C(Br)=C1 HNVVROFWONXXGO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000009835 boiling Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
QDKIFIYGNKHERN-UHFFFAOYSA-N 4-(bromomethyl)-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(CBr)C=C1OC1=CC=CC=C1 QDKIFIYGNKHERN-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
238000010626 work up procedure Methods 0.000 description 6
AZLURTMGDNMKNK-UHFFFAOYSA-N 2-bromo-1-fluoro-4-(phenylmethoxymethyl)benzene Chemical compound C1=C(Br)C(F)=CC=C1COCC1=CC=CC=C1 AZLURTMGDNMKNK-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 5
239000000243 solution Substances 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000002585 base Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
239000011734 sodium Chemical group 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
KPKIKQUFZNQNRL-UHFFFAOYSA-N 1-fluoro-2-phenoxy-4-(phenoxymethyl)benzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1COC1=CC=CC=C1 KPKIKQUFZNQNRL-UHFFFAOYSA-N 0.000 description 3
YUCJSTYDUCDPDJ-UHFFFAOYSA-N 2-bromo-1-fluoro-4-(phenoxymethyl)benzene Chemical compound C1=C(Br)C(F)=CC=C1COC1=CC=CC=C1 YUCJSTYDUCDPDJ-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
AIOKJVVAYNKWQP-UHFFFAOYSA-N 3-bromo-4-fluorobenzoyl fluoride Chemical compound FC(=O)C1=CC=C(F)C(Br)=C1 AIOKJVVAYNKWQP-UHFFFAOYSA-N 0.000 description 3
GIQURHRJQIPDKM-UHFFFAOYSA-N 4-fluorobenzoyl fluoride Chemical compound FC(=O)C1=CC=C(F)C=C1 GIQURHRJQIPDKM-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000005661 deetherification reaction Methods 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
229960004592 isopropanol Drugs 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
229940031826 phenolate Drugs 0.000 description 3
229910052700 potassium Chemical group 0.000 description 3
239000011591 potassium Chemical group 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
YJPMOACEQSBJFU-UHFFFAOYSA-N 1-fluoro-2-phenoxy-4-(phenylmethoxymethyl)benzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1COCC1=CC=CC=C1 YJPMOACEQSBJFU-UHFFFAOYSA-N 0.000 description 2
NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 2
ZRWSODQPUJMFRV-UHFFFAOYSA-N 2-bromo-4-(bromomethyl)-1-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1Br ZRWSODQPUJMFRV-UHFFFAOYSA-N 0.000 description 2
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Chemical group 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
239000005457 ice water Substances 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
239000001095 magnesium carbonate Substances 0.000 description 2
229910000021 magnesium carbonate Inorganic materials 0.000 description 2
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 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
239000011698 potassium fluoride Substances 0.000 description 2
235000003270 potassium fluoride Nutrition 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ILKFYEKKPVEUOK-UHFFFAOYSA-N 1-fluoro-4-methyl-2-phenoxybenzene Chemical compound CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 ILKFYEKKPVEUOK-UHFFFAOYSA-N 0.000 description 1
NJKXWUNZKLQLRV-UHFFFAOYSA-N 2-(bromomethyl)-5-fluoro-5-phenoxycyclohexa-1,3-diene Chemical compound FC1(CC=C(CBr)C=C1)OC1=CC=CC=C1 NJKXWUNZKLQLRV-UHFFFAOYSA-N 0.000 description 1
WVZWBCYWQAZDTK-UHFFFAOYSA-N 2-bromo-4-(chloromethyl)-1-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1Br WVZWBCYWQAZDTK-UHFFFAOYSA-N 0.000 description 1
UPABIPOBMNDDGQ-UHFFFAOYSA-N 2-fluorobenzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1F UPABIPOBMNDDGQ-UHFFFAOYSA-N 0.000 description 1
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
PEVJJRDDXKCISU-UHFFFAOYSA-N P(Cl)(Cl)(Cl)(Cl)Cl.[P] Chemical compound P(Cl)(Cl)(Cl)(Cl)Cl.[P] PEVJJRDDXKCISU-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
OCXGTPDKNBIOTF-UHFFFAOYSA-N dibromo(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 OCXGTPDKNBIOTF-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 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
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
- C07C43/1742—Unsaturated ethers containing halogen containing six-membered aromatic rings with halogen atoms bound to the aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD223395A 1979-08-22 1980-08-19 Verfahren zur herstellung neuer 4-fluor-3-phenoxy-benzyl-ether DD153203A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2933985A DE2933985A1 (de)	1979-08-22	1979-08-22	Neue 4-fluor-3-phenoxy-benzyl-ether und verfahren zu deren herstellung sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung

Publications (1)

Publication Number	Publication Date
DD153203A5 true DD153203A5 (de)	1981-12-30

Family

ID=6079046

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD223395A DD153203A5 (de)	1979-08-22	1980-08-19	Verfahren zur herstellung neuer 4-fluor-3-phenoxy-benzyl-ether

Country Status (7)

Country	Link
US (2)	US4326087A (fr)
EP (2)	EP0024612B1 (fr)
JP (1)	JPS5630937A (fr)
BR (1)	BR8005299A (fr)
DD (1)	DD153203A5 (fr)
DE (2)	DE2933985A1 (fr)
DK (1)	DK359080A (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2933985A1 (de) *	1979-08-22	1981-04-09	Bayer Ag, 5090 Leverkusen	Neue 4-fluor-3-phenoxy-benzyl-ether und verfahren zu deren herstellung sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung
DE3036967A1 (de) *	1980-10-01	1982-05-13	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 3-brom-4-fluor-benzylalkohol und neue zwischenprodukte hierfuer
EP0084194B1 (fr) *	1982-01-14	1986-04-30	MERCK PATENT GmbH	Mélanges de cristaux liquides
US4648996A (en) *	1984-07-27	1987-03-10	Hoffmann-La Roche Inc.	Phenyl substituted-2,4,6,8-nonatetraenoic acid
US4780251A (en) *	1984-07-27	1988-10-25	Hoffman-La Roche Inc.	Phenyl substituted-2,4,6,8-nonatetraenoic acid
ZA854828B (en) *	1984-07-27	1986-03-26	Hoffmann La Roche	Phenyl nonatetraenoic acid derivatives
US4883613A (en) *	1984-07-27	1989-11-28	Hoffmann-La Roche Inc.	Phenyl substituted-2,4,6,8-nonatetraenoic acid
US4883614A (en) *	1984-07-27	1989-11-28	Hoffman-La Roche Inc.	Phenyl substituted-2,4,6,8-nonatetraenoic acid
US4894480A (en) *	1984-07-27	1990-01-16	Hoffmann-La Roche Inc.	Phenyl substituted-2,4,6,8-nonatetraenoic acid
DE3602169A1 (de) *	1986-01-22	1987-07-23	Schering Ag	Neue alkan- und alkoxyalkanderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel
GB8614002D0 (en) *	1986-06-09	1986-07-16	Ici Plc	Halogenated diphenyl ether derivatives
US4798912A (en) *	1986-11-19	1989-01-17	Ciba-Geigy Corporation	Substituted phenoxybenzyl-(Dihalodimethylcyclopropyl-methyl)ethers
DE3901706A1 (de) *	1988-05-17	1989-11-30	Bayer Ag	Halogensubstituierte phenoxybenzyl(thi)ol-derivate
CN1047377C (zh) *	1996-12-17	1999-12-15	阜新特种化学股份有限公司	2－氟－4－溴甲苯、2－氟－4－溴苄基溴及其2－氟－4－溴苄基溴制备方法
DE50000412D1 (de)	1999-01-13	2002-10-02	Basf Ag	Azadioxacycloalkene und ihre verwendung zur bekämpfung von schadpilzen und tierischen schädlingen

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2121723A (en) *		1938-06-21		Aralkyl ethers
US2073010A (en) *		1937-03-09		halogenated aralkyl-aryl ethers
US2121724A (en) *		1938-06-21		aralkyl ethers of ethyl-phenol
US2109514A (en) *		1938-03-01		Aralkyl ethers of di-alkyl phenols
GB1460295A (en) *	1973-06-01	1976-12-31	Boots Co Ltd	Biphenyls and diphenyl ethers
JPS5085986A (fr) *	1973-12-03	1975-07-10
DE2433066C2 (de) *	1974-07-10	1982-12-23	Hoechst Ag, 6000 Frankfurt	4-Trifluormethyl-4'-hydroxy-diphenyläther und Verfahren zu ihrer Herstellung
DE2709264C3 (de) *	1977-03-03	1982-01-21	Bayer Ag, 5090 Leverkusen	Substituierte Phenoxybenzyloxycarbonylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide sowie neue Zwischenprodukte
GB2010837B (en) *	1977-12-22	1982-07-28	Croda Synthetic Chem Ltd	Process for preparing aralkyl halides
DE2961921D1 (en) *	1978-01-30	1982-03-11	Shell Int Research	Process for the manufacture of a mixture of 3-phenoxybenzyl bromide and 3-phenoxybenzal bromide
DE2837525A1 (de) *	1978-08-28	1980-03-20	Bayer Ag	Verfahren zur herstellung von 4- fluoro-3-phenoxy-toluol
DE2933985A1 (de) *	1979-08-22	1981-04-09	Bayer Ag, 5090 Leverkusen	Neue 4-fluor-3-phenoxy-benzyl-ether und verfahren zu deren herstellung sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung
DE2933979A1 (de) *	1979-08-22	1981-03-12	Bayer Ag, 5090 Leverkusen	Neue 4-fluor-3-phenoxy-benzaldehydacetale und verfahren zu deren herstellung sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung.

1979
- 1979-08-22 DE DE2933985A patent/DE2933985A1/de not_active Withdrawn
1980
- 1980-07-30 US US06/173,544 patent/US4326087A/en not_active Expired - Lifetime
- 1980-08-09 EP EP80104715A patent/EP0024612B1/fr not_active Expired
- 1980-08-09 EP EP82101152A patent/EP0059365A3/fr not_active Withdrawn
- 1980-08-09 DE DE8080104715T patent/DE3065163D1/de not_active Expired
- 1980-08-19 DD DD223395A patent/DD153203A5/de unknown
- 1980-08-20 JP JP11355280A patent/JPS5630937A/ja active Pending
- 1980-08-21 DK DK359080A patent/DK359080A/da not_active Application Discontinuation
- 1980-08-21 BR BR8005299A patent/BR8005299A/pt unknown
1981
- 1981-08-04 US US06/289,854 patent/US4381412A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0059365A2 (fr)	1982-09-08
JPS5630937A (en)	1981-03-28
DE2933985A1 (de)	1981-04-09
EP0024612B1 (fr)	1983-10-05
DE3065163D1 (en)	1983-11-10
EP0059365A3 (fr)	1983-01-05
US4381412A (en)	1983-04-26
EP0024612A3 (en)	1981-06-17
DK359080A (da)	1981-02-23
BR8005299A (pt)	1981-03-04
US4326087A (en)	1982-04-20
EP0024612A2 (fr)	1981-03-11

Publication	Publication Date	Title
DD153203A5 (de)	1981-12-30	Verfahren zur herstellung neuer 4-fluor-3-phenoxy-benzyl-ether
EP0024624B1 (fr)	1984-07-04	Acétals de 4-fluoro-3-phénoxy-benzaldéhyde, procédé pour leur préparation et leurs produits intermédiaires
DE3816120A1 (de)	1989-11-23	Verfahren zur herstellung von unsymmetrischen biarylverbindungen
EP0008734B1 (fr)	1981-07-29	Procédé de préparation de 4-fluor-3-phénoxytoluène
EP0607824A2 (fr)	1994-07-27	Procédé pour la fabrication de fluorures de benzényle, chlorures de benzényles et chlorures de benzoyle multiple halogénés et chlorures de benzényle et benzoyle trihalogénés
EP0006205B1 (fr)	1982-09-22	Procédé pour la préparation de dérivés d'acides chlorostyrène cyclopropane carboxyliques
EP1191012B1 (fr)	2007-01-17	Procédé de préparation d'aldéhydes benzéniques fluorés
DE2536504C3 (de)	1985-06-27	Verfahren zur Herstellung von Halogendienen
DE3039999A1 (de)	1982-05-27	N-alkylierte formamide, verfahren zu ihrer herstellung und ihre verwendung
EP0048914A1 (fr)	1982-04-07	Procédé de préparation d'alcool 3-bromo-4-fluorobenzylique, produits intermédiaires et procédé de préparation de ces produits intermédiaires
DD261601A5 (de)	1988-11-02	Verfahren zur herstellung von 2,3-dihydrofuranverbindungen
DD152537A5 (de)	1981-12-02	Verfahren zur herstellung von 4-fluor-3-phenoxy-toluol
DE4225763A1 (de)	1994-02-10	Verfahren zur Herstellung von Halogenaromaten
DE3026959A1 (de)	1982-02-04	Verfahren zur herstellung von 3-brom-4-fluor-benzaldehyd-(-acetalen) und neue zwischenprodukte hierfuer
EP0084128B1 (fr)	1987-01-21	Procédé de préparation d'alcoylbenzènes substitués par des radicaux fluorés
EP0347690B1 (fr)	1992-10-21	Procédé de préparation de dérivés du benzène et dérivés du benzène
EP0341478A2 (fr)	1989-11-15	Procédé de préparation de la 2,3-dichloro-5-acétylpyridine
DE3129651A1 (de)	1983-02-17	Verfahren zur herstellung von 3-brom-4-fluor-benzaldehyd
DE3880072T2 (de)	1993-08-05	N-phenyl-2,2,6,6-tetrahalogencyclohexanimin und verfahren zur herstellung von derivaten des 2,2,6,6-tetrahalogencyclohexanimins und von derivaten des 2,6-dihalogenanilins.
DE60007137T2 (de)	2004-09-09	Verfahren zur herstellung von 2-arylvinylalkylethern und 1,4-diaryl-2-fluor-2-butenen
CH650488A5 (de)	1985-07-31	Verfahren zur herstellung des m-phenoxy-benzyl-alkohols.
EP0251115B1 (fr)	1991-08-21	Procédé pour la fabrication d'arylcétones bêta-halovinyles et bêta, bêta-dihaloéthyles
DD261599A5 (de)	1988-11-02	Verfahren zur herstellung von verbindungen mit triazol- oder imidazol und tetrahydrofurangruppe
EP0017882A1 (fr)	1980-10-29	Procédé de préparation de l'acide 3-phénoxy-4-fluoro-benzoique
DE3808115A1 (de)	1989-09-28	Verfahren zur herstellung von 6-acetyl-3-amino-2,4-dihalogen-pyridin