Abstract:
PURPOSE:To obtain the title compound in one step in high yield, without using highly toxic phosgene, by the reaction of an aromatic carboxylic acid derivative with CO and Cl2, using a catalyst, e.g. phosphine sulfide. CONSTITUTION:An aromatic carboxylic acid or its anhydride, CO and Cl2 are made to react in a stoichiometric amount in a solvent at 60-200 deg.C in the presence of a phosphine sulfide or selenide of formula I (R=C1-11 alkyl, C6-14 aryl etc.; X=S or Se), e.g. tributylphosphine sulfide or triphenylphosphine selenide, to give the corresponding aromatic carboxylic acid chloride. The amount of the above catalyst is preferably in the range of 1/200-1/15mol based on the product of the number of mols of the aromatic carboxylic acid (anhydride) and the number of the carboxyl or its anhydride groups in one molecule of the acid or its anhydride.
Abstract:
PURPOSE:To obtain the title compound in one step in high yield, without using phosgene., by the reaction of an aromatic carboxylic acid derivative with CO and Cl2, using a specific catalyst, e.g. phosphine oxide. CONSTITUTION:An aromatic carboxylic acid or its acid anhydride, Co and Cl2 are made to react in a solvent at 60-200 deg.C in the presence of a phosphine oxide of formula I (R=C6-14 aryl, C7-14 aralkyl; provided that at least one of the three Rs is aryl or aralkyl mentioned above), e.g. methyldiphenylphosphine oxide, and/or a phosphonous dichloride of formula II, e.g. triphenylphosphosphonous dichloride, to give the corresponding aromatic carboxylic acid chloride. The amount of the above catalyst is preferably in the range of 1/200-1/50mol based on the product of the number of moles the aromatic carboxylic acid and the number of the carboxyl groups contained in one molecule of the acid.