CA1208655A - Procede a solvant unique pour la preparation d'esters de 3,5-dibromo-4-hydroxy-benzonitrile - Google Patents

Procede a solvant unique pour la preparation d'esters de 3,5-dibromo-4-hydroxy-benzonitrile

Info

Publication number: CA1208655A
Authority: CA; Canada
Prior art keywords: dibromo; hydroxybenzonitrile; cyanophenol; acid halide; reacting
Prior art date: 1984-02-29
Legal status (The legal status 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 status listed.): Expired

Application number

CA000448496A

Other languages

English (en)

Inventor

Richard E. Sheads

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1984-02-29

Filing date

1984-02-29

Publication date

1986-07-29

1984-02-29 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1984-02-29 Priority to CA000448496A priority Critical patent/CA1208655A/fr

1986-07-29 Application granted granted Critical

1986-07-29 Publication of CA1208655A publication Critical patent/CA1208655A/fr

Status Expired legal-status Critical Current

Links

UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 title claims abstract description 21
150000002148 esters Chemical class 0.000 title claims abstract description 18
238000000034 method Methods 0.000 title claims description 35
239000002904 solvent Substances 0.000 title abstract description 15
238000002360 preparation method Methods 0.000 title description 4
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 claims abstract description 17
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims abstract description 12
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims description 20
125000001931 aliphatic group Chemical group 0.000 claims description 18
150000004820 halides Chemical class 0.000 claims description 15
150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
-1 aromatic acid halide Chemical class 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
239000012429 reaction media Substances 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000005711 Benzoic acid Substances 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
150000001559 benzoic acids Chemical group 0.000 claims description 2
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical group CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical group CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 claims 1
KLUSIGFSJQSFKX-UHFFFAOYSA-N 1,1,1-trichloroethane;1,1,2-trichloroethane Chemical compound CC(Cl)(Cl)Cl.ClCC(Cl)Cl KLUSIGFSJQSFKX-UHFFFAOYSA-N 0.000 claims 1
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 abstract description 7
230000031709 bromination Effects 0.000 abstract description 5
238000005893 bromination reaction Methods 0.000 abstract description 5
238000005886 esterification reaction Methods 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003839 salts Chemical group 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
239000005489 Bromoxynil Substances 0.000 description 2
159000000032 aromatic acids Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
YRSSHOVRSMQULE-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzonitrile Chemical compound OC1=C(Cl)C=C(C#N)C=C1Cl YRSSHOVRSMQULE-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000448496A 1984-02-29 1984-02-29 Procede a solvant unique pour la preparation d'esters de 3,5-dibromo-4-hydroxy-benzonitrile Expired CA1208655A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000448496A CA1208655A (fr)	1984-02-29	1984-02-29	Procede a solvant unique pour la preparation d'esters de 3,5-dibromo-4-hydroxy-benzonitrile

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000448496A CA1208655A (fr)	1984-02-29	1984-02-29	Procede a solvant unique pour la preparation d'esters de 3,5-dibromo-4-hydroxy-benzonitrile

Publications (1)

Publication Number	Publication Date
CA1208655A true CA1208655A (fr)	1986-07-29

Family

ID=4127298

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000448496A Expired CA1208655A (fr)	1984-02-29	1984-02-29	Procede a solvant unique pour la preparation d'esters de 3,5-dibromo-4-hydroxy-benzonitrile

Country Status (1)

Country	Link
CA (1)	CA1208655A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115605460A (zh) *	2020-04-29	2023-01-13	普莱希科公司（Us）	杂环化合物的合成
CN116573997A (zh) *	2023-03-28	2023-08-11	黄冈市楚雄化工股份有限公司	环氧乙烷在抑制乙醛聚合中的应用
CN118795118A (zh) *	2024-09-13	2024-10-18	中电数科科技有限公司	一种智慧农业用土壤监测装置

1984
- 1984-02-29 CA CA000448496A patent/CA1208655A/fr not_active Expired

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115605460A (zh) *	2020-04-29	2023-01-13	普莱希科公司（Us）	杂环化合物的合成
CN116573997A (zh) *	2023-03-28	2023-08-11	黄冈市楚雄化工股份有限公司	环氧乙烷在抑制乙醛聚合中的应用
CN118795118A (zh) *	2024-09-13	2024-10-18	中电数科科技有限公司	一种智慧农业用土壤监测装置
CN118795118B (zh) *	2024-09-13	2024-12-24	中电数科科技有限公司	一种智慧农业用土壤监测装置

Legal Events

Date	Code	Title	Description
2004-02-29	MKEX	Expiry

Publication	Publication Date	Title
JPS59144734A (ja)	1984-08-18	親水性フエノ−ルエステル誘導体の合成法
US4439368A (en)	1984-03-27	One solvent process for preparation of esters of 3,5-dibromo-4-hydroxybenzonitrile
CA1208655A (fr)	1986-07-29	Procede a solvant unique pour la preparation d'esters de 3,5-dibromo-4-hydroxy-benzonitrile
HU193589B (en)	1987-10-28	Process for preparing fluorinated phtaloyl- and terephtaloyl compounds
US4436665A (en)	1984-03-13	Two solvent process for preparation of esters of 3,5-dibromo-4-hydroxybenzonitrile
EP0795546B1 (fr)	2004-06-02	Formamides N,N-disubstituées comme catalyseurs d'halogénation
GB2155008A (en)	1985-09-18	One solvent process for preparation of esters of 3,5-dibromo-4-hydroxybenzonitrile
US6015911A (en)	2000-01-18	Process for preparing 1-alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole and related compounds
US4709081A (en)	1987-11-24	Process for the preparation of diphenyl ether derivatives
JPS61260041A (ja)	1986-11-18	６−（低級）アルコキシ−１−ナフトエ酸類およびその対応するそれらのエステルの製造方法ならびに６−（低級）アルコキシ−５−ハロ−１−ナフトエ酸類および対応するそれらのエステルの製造方法
JPH11501314A (ja)	1999-02-02	スチルベンジカルボン酸のエステル類の調製方法
NZ207314A (en)	1986-09-10	The preparation of 3,5-dibromo-4-hydroxybenzonitrile esters from 4-cyanophenol
US5475165A (en)	1995-12-12	Trifluoromethylation process
KR100266926B1 (ko)	2000-09-15	2,4-디클로로-5-플루오로벤조니트릴의 제조방법
JP3431218B2 (ja)	2003-07-28	クロマンカルボン酸誘導体の製法
JP2786315B2 (ja)	1998-08-13	塩素化ジフエニルエーテルの製造方法
JP2934776B2 (ja)	1999-08-16	ピバリン酸ハロメチルエステル類の製造法
EP0600714A1 (fr)	1994-06-08	Procédé de production de l'anhydride 0,0'-diacyltartrique et procédé de production d'acide 0,0'-diacyltartrique
US4339601A (en)	1982-07-13	Terephthalic acid derivatives and process for preparing them
US6111130A (en)	2000-08-29	Process for the preparation of trifluoromethyl containing derivatives
US4252979A (en)	1981-02-24	Terephthalic acid derivatives
FR2560872A1 (fr)	1985-09-13	Procede utilisant un seul solvant pour la preparation d'esters de 3,5-dibromo-4-hydroxybenzonitrile
WO1994021589A1 (fr)	1994-09-29	Procede de preparation d'anhydride citraconique
JPH03127753A (ja)	1991-05-30	４―クロロ―４′―ヒドロキシベンゾフェノン類の製造法
JPH0243745B2 (ja)	1990-10-01	Torikuroromechirukinokisarinruioyobisonoseizohoho