Preparation method of 3,5-di (trifluoromethyl) benzoyl chloride and new 3,5-di trihalomethyl benzoylate A and 3,5-dimethyl benzoylate A

A technology of benzoyl chloride and trifluoromethyl, used in the preparation of 3,5-bis(trifluoromethyl)benzoyl chloride and new 3,5-bis(trihalomethyl)- and 3, In the field of 5-dimethylbenzoyl halide, it can solve problems such as huge expenses
CN1216028CInactive Publication Date: 2005-08-24LANXESS DEUTDCHLAND GMBH
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
LANXESS DEUTDCHLAND GMBH
Publication Date
2005-08-24
Estimated Expiration
Not applicable · inactive patent

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Abstract

Preparation of 3,5-bis-(trifluoromethyl)-benzoyl chlorides (I) involves converting a 3,5-dimethyl-benzoic acid (V) into the acid chloride (IV), subjecting the side-chains to radical chlorination, fluorinating with anhydrous hydrogen fluoride and / or antimony pentafluoride to give a 3,5-bis-(trifluoromethyl)-benzoyl fluoride and reacting with silicon tetrachloride in presence of another Lewis acid. Preparation of 3,5-bis-(trifluoromethyl)-benzoyl chlorides of formula (I) involves: (1) converting a 3,5-dimethyl-benzoic acid of formula (V) into the corresponding acid chloride of formula (IV); (2) subjecting the side-chains to complete radical chlorination to give a 3,5-bis-(trichloromethyl)-benzoyl chloride of formula (III); (3) fluorinating with anhydrous hydrogen fluoride and / or antimony pentafluoride to give a 3,5-bis-(trifluoromethyl)-benzoyl fluoride of formula (II); and (4) reacting with silicon tetrachloride in presence of another Lewis acid. [Image] X : H, F or Cl. Independent claims are included for the intermediates (III; X = F or Cl) and (IV; X = F or Cl) as new compounds.
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Description

technical field

[0001] The present invention relates to a process for the preparation of 3,5-bis(trifluoromethyl)benzoyl chloride from the corresponding 3,5-dimethylbenzoic acid and novel 3,5-bis( Trihalomethyl)- and 3,5-dimethylbenzoyl halides. Hereinafter, 3,5-bis(trifluoromethyl)-benzoyl chloride is also referred to as BTBs. Background technique

[0002] BTBs are intermediates in the preparation of pharmaceutical and agrochemical active ingredients as well as photoresist ingredients.

[0003] The preparation of BTBs from the corresponding 3,5-bis(trifluoromethyl)benzoic acid by chlorination is known (see, e.g., J.Med.Chem. 38 , 3106 (1995)). This acid can be obtained by two different methods, namely,

[0004] a) Metallization of 1-bromo-3,5-bis(trifluoromethyl)benzene with magnesium or lithium (see, Bull.Soc.Chim.Fr. 1962 (587) and Chem. Ber. 129 , 233 (1996)), followed by reaction with carbon dioxide, or with carbon monoxide and water in the presence of a palladiu...

Claims

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