METHOD FOR PRODUCING 3,5-BIS(TRIFLUOROMETHYL)BENZOYL CHLORIDE AND NEW 3,5-BIS(TRIHALOGENOMETHYL)- AND 3,5- DIMETHYLBENZOYL HALIDES

    公开(公告)号:JP2001294551A

    公开(公告)日:2001-10-23

    申请号:JP2001021329

    申请日:2001-01-30

    Applicant: BAYER AG

    Abstract: PROBLEM TO BE SOLVED: To provide a method for producing a 3,5-bis(trifluoromethyl)benzoyl chloride from a readily available starting material, surely practicable on an industrial scale, and to obtain intermediate(s) formed during the above process. SOLUTION: This method comprises the following steps: a 3,5-dimethylbenzoic acid is converted to the corresponding acid chloride, which, in turn, is completely chlorinated in a free radical fashion at the side chains to form the corresponding 3,5-bis(trichloromethyl)benzoyl chloride, which is then fluorinated with anhydrous hydrogen fluoride and/or antimony pentafluoride to produce the corresponding 3,5-bis(trifluoromethyl)benzoyl fluoride, which, in turn, is reacted in the presence of silicon tetrachloride and an additional Lewis acid to obtain the objective compound of the general formula I (X is H, F or Cl). By the way, some of the 3,5-bis(trihalogenomethyl)- and 3,5-dimethylbenzoyl compounds as intermediates are new compounds.

    METHODOF OBTAINING [BIS-(TRIFLUOROMETHYL)-PHENYL]-ACETIC ACIDS AND THEIR ALKYL ESTERS AS WELL AS DIALKYL ESTERS OF [BIS-(TRIFLUOROMETHYL)-PHENYL]-MALONIC ACIDS

    公开(公告)号:PL341973A1

    公开(公告)日:2001-02-26

    申请号:PL34197300

    申请日:2000-08-11

    Applicant: BAYER AG

    Abstract: Preparation of (bis-(trifluoromethyl)-phenyl)-acetic acids (I) involves (a) reacting a bromo- or iodo-bis-(trifluoromethyl)-benzene (II) with a di-(1-4C alkyl) malonate (III) in presence of a deprotonating reagent and a copper salt, then (b) saponifying and decarboxylating the product in a basic medium. Also new are a method for preparing dialkyl phenylmalonates (IV) and alkyl phenylacetates (V) using step (a); and the compounds (IV). Independent claims are included for: (i) the preparation of (bis-(trifluoromethyl)-phenyl)-acetic acid esters, by step (a) as above followed by cooling the reaction mixture, acidifying to pH 5-9, separating the solids, washing the residue with an ether or alcohol and recovering product from the combined filtrate and washings by distillation under reduced pressure; (ii) the preparation of a mixture of dialkyl phenylmalonates of formula (IV) and alkyl phenylacetates of formula (V), by step (a) as above followed (before saponification and complete decarboxylation) by treating the reaction mixture with water and acid, heating and working up the mixture by extraction and distillation; (iii) the preparation of (IV) by working up the mixture obtained in (ii) by column chromatography, fractional distillation or thin film distillation; (iv) the preparation of (V) by working up the mixture obtained in (ii) by distillation under reduced pressure; and (v) (IV) as new compounds. R = 1-4C alkyl.

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