IE72493B1 - Process for the preparation of 2,4-dichloro-5-fluoro-benzoic acid - Google Patents
Process for the preparation of 2,4-dichloro-5-fluoro-benzoic acidInfo
- Publication number
- IE72493B1 IE72493B1 IE238085A IE238085A IE72493B1 IE 72493 B1 IE72493 B1 IE 72493B1 IE 238085 A IE238085 A IE 238085A IE 238085 A IE238085 A IE 238085A IE 72493 B1 IE72493 B1 IE 72493B1
- Authority
- IE
- Ireland
- Prior art keywords
- dichloro
- fluoro
- process according
- preparation
- benzoic acid
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 19
- KZCWJHUTTSVCRO-UHFFFAOYSA-N 2,4-dichloro-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(Cl)C=C1Cl KZCWJHUTTSVCRO-UHFFFAOYSA-N 0.000 title abstract description 4
- 230000010933 acylation Effects 0.000 claims abstract description 13
- 238000005917 acylation reaction Methods 0.000 claims abstract description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 11
- BDJZCCWUSOZUQG-UHFFFAOYSA-N 2,4-dichloro-1-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1Cl BDJZCCWUSOZUQG-UHFFFAOYSA-N 0.000 claims abstract description 7
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012346 acetyl chloride Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000005708 Sodium hypochlorite Substances 0.000 claims abstract description 6
- 239000003085 diluting agent Substances 0.000 claims abstract description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 238000002955 isolation Methods 0.000 claims abstract description 4
- FAKJFAMIABOKBW-UHFFFAOYSA-N 1-(2,4-dichloro-5-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC(F)=C(Cl)C=C1Cl FAKJFAMIABOKBW-UHFFFAOYSA-N 0.000 claims abstract 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- 238000007796 conventional method Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- -1 aliphatic carboxylic acid halides Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ANXOZOZWHNFHPZ-UHFFFAOYSA-N 1-(2,2-difluoro-1-phenylethenyl)-4-fluorobenzene Chemical compound C=1C=C(F)C=CC=1C(=C(F)F)C1=CC=CC=C1 ANXOZOZWHNFHPZ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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 1
- MIZKCMSSYVUZKD-UHFFFAOYSA-N 2-chloro-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1Cl MIZKCMSSYVUZKD-UHFFFAOYSA-N 0.000 description 1
- YOMBUJAFGMOIGS-UHFFFAOYSA-N 2-fluoro-1-phenylethanone Chemical compound FCC(=O)C1=CC=CC=C1 YOMBUJAFGMOIGS-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843435392 DE3435392A1 (de) | 1984-09-27 | 1984-09-27 | Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoesaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE852380L IE852380L (en) | 1986-03-27 |
| IE72493B1 true IE72493B1 (en) | 1997-04-23 |
Family
ID=6246450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE238085A IE72493B1 (en) | 1984-09-27 | 1985-09-26 | Process for the preparation of 2,4-dichloro-5-fluoro-benzoic acid |
Country Status (21)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4791225A (en) * | 1986-01-20 | 1988-12-13 | Kyorin Pharmaceutical Co., Ltd. | Halogenobenzoic acid derivatives and their preparation |
| DE3641099A1 (de) * | 1986-12-02 | 1988-06-09 | Hoechst Ag | Verfahren zur herstellung von 4-(2'-chlorethyl)benzoesaeure |
| DE3840371A1 (de) * | 1988-11-30 | 1990-05-31 | Lentia Gmbh | Verfahren zur herstellung von 2,4,5-trifluorbenzoesaeure |
| US4996355A (en) * | 1989-04-14 | 1991-02-26 | Mallinckrodt, Inc. | Novel intermediates for the production of 2,4,5-trifluorobenzoyl fluoride |
| DE3925036A1 (de) * | 1989-07-28 | 1991-01-31 | Riedel De Haen Ag | Verfahren zur herstellung von fluorierten benzoesaeuren |
| GB9107684D0 (en) * | 1991-04-11 | 1991-05-29 | Berge Richard | Panel system |
| DE19617558A1 (de) * | 1996-05-02 | 1997-11-06 | Hoechst Ag | Verfahren zur Herstellung von 4,5-Dichlor-2-methylbenzoesäure |
| DE19733243A1 (de) | 1997-08-01 | 1999-02-04 | Bayer Ag | Verfahren zur Herstellung von 3-Cyano-2,4-dihalogen-5-fluor-benzoesäure |
| RU2155185C1 (ru) * | 1999-03-24 | 2000-08-27 | Новосибирский институт органической химии им. Н.Н. Ворожцова СО РАН | Способ получения частично фторированных бензойных кислот |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2412855C2 (de) * | 1974-03-18 | 1983-03-31 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Carbonsäuren |
| DE3035355A1 (de) * | 1980-09-19 | 1982-04-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-brom-4-fluor-benzoesaeure |
| DE3248506A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(alkyl-1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3248505A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(4- (oxoalkyl)-1-piperazinyl/-3-chinolincarbonsaeuren und ihre derivate, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
-
1984
- 1984-09-27 DE DE19843435392 patent/DE3435392A1/de not_active Withdrawn
-
1985
- 1985-09-11 UA UA3950798A patent/UA8020A1/uk unknown
- 1985-09-11 SU SU853950798A patent/SU1470175A3/ru active
- 1985-09-13 NO NO853605A patent/NO159080C/no not_active IP Right Cessation
- 1985-09-17 PT PT81144A patent/PT81144B/pt not_active IP Right Cessation
- 1985-09-18 EP EP85111789A patent/EP0176026B1/de not_active Expired
- 1985-09-18 DE DE8585111789T patent/DE3561054D1/de not_active Expired
- 1985-09-23 IL IL76466A patent/IL76466A/xx not_active IP Right Cessation
- 1985-09-24 JP JP60209034A patent/JPH0647568B2/ja not_active Expired - Lifetime
- 1985-09-24 KR KR1019850006988A patent/KR910008936B1/ko not_active Expired
- 1985-09-24 NZ NZ213599A patent/NZ213599A/en unknown
- 1985-09-25 CA CA000491506A patent/CA1255330A/en not_active Expired
- 1985-09-25 AU AU47924/85A patent/AU569176B2/en not_active Ceased
- 1985-09-25 FI FI853686A patent/FI86413C/fi not_active IP Right Cessation
- 1985-09-26 DD DD85281050A patent/DD239591A5/de not_active IP Right Cessation
- 1985-09-26 ES ES547345A patent/ES8605462A1/es not_active Expired
- 1985-09-26 PH PH32852A patent/PH24252A/en unknown
- 1985-09-26 HU HU853691A patent/HU193345B/hu not_active IP Right Cessation
- 1985-09-26 GR GR852346A patent/GR852346B/el unknown
- 1985-09-26 IE IE238085A patent/IE72493B1/en not_active IP Right Cessation
- 1985-09-26 DK DK436685A patent/DK166411B1/da not_active IP Right Cessation
- 1985-09-26 ZA ZA857432A patent/ZA857432B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0140875B1 (ko) | 피라졸 밀 이들의 유도체를 제조하는 방법 | |
| IE72493B1 (en) | Process for the preparation of 2,4-dichloro-5-fluoro-benzoic acid | |
| JP4482162B2 (ja) | 置換ピラゾールの製造方法 | |
| KR0174272B1 (ko) | 3-메틸피라졸의 제조방법 | |
| US4434292A (en) | Process for the preparation of pyrazole | |
| JPH0248548B2 (enrdf_load_stackoverflow) | ||
| JPH0329780B2 (enrdf_load_stackoverflow) | ||
| AU772981B2 (en) | Method for producing 4-(heteroaryl-methyl)-halogen-1(2H)-phthalazinones | |
| AU703688B2 (en) | Process for producing 3,5-diaryl pyrazolene | |
| JPH0134219B2 (enrdf_load_stackoverflow) | ||
| JP4641667B2 (ja) | １−メチル−５−ハイドロキシピラゾールの製造法 | |
| SU497776A3 (ru) | Способ получени производных диазепина | |
| US5162539A (en) | Preparation of 2-alkylthio-1,3,4-thiadiazoles | |
| US4292431A (en) | Process for the production of hydroxymethylimidazoles | |
| US4393232A (en) | Preparation of 3-bromo-4-fluoro-benzoic acid | |
| JPS6242962A (ja) | アジドスルホニル安息香酸の製造法 | |
| US5200556A (en) | Process for the preparation of 3,4,6-trifluorophthalic acid and the anhydride thereof | |
| US3654292A (en) | Manufacture of 3 5-dichloro-2 6-difluoro - 4 - hydroxypyridine and salts thereof | |
| JPH0481576B2 (enrdf_load_stackoverflow) | ||
| SU1721051A1 (ru) | Способ получени 2-галоидпроизводных фурана | |
| JP2547089B2 (ja) | カルボン酸類の製法 | |
| KR100278967B1 (ko) | 오르쏘-디플루오로벤조산 유도체의 제조방법 | |
| CA2209486C (en) | Preparation of 3,5-diarylpyrazoles | |
| JPH04297450A (ja) | チオリンゴ酸の製造方法 | |
| KR930000664B1 (ko) | 퀴놀론유도체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |