Imidazole → alpha-(2,6-Dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanol

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Reaction Steps

To a suspension of 21 g of α-(2,6-dimethyl-4-carboxyphenyl)-2-chloro-5-iodobenzenemethanol, 5.1 g of imidazole, 13.8 g of potassium carbonate and 120 ml of dimethylformamide are added 0.4 g of potassium fluoride and 0.4 g of copper powder, and the mixture is stirred at 135°-140° C. for 30 hours. After cooling, to the reaction mixture is added 240 ml of water and 0.45 g of sodium sulfide trihydrate. The whole mixture is stirred for 30 minutes. The precipitated copper sulfide is filtered with sellaite under reduced pressure and the filtrate is adjusted to pH 4 with concentrated hydrochloric acid under heating and stirring. The precipitated crystals are collected by filtration, washed with water and then dried. Recrystallization from dimethylformamide gives α-(2,6-dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanol, melting at 318°-320° C. with decomposition, as white crystals in high yield.

Provenance & Evidence