Aniline → 7-Fluoro-1-phenyl-5-trifluoromethylbenzimidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of aniline (1.12 ml, 12.3 mmol) and 2,3-difluoro-1-nitro-5-trifluoromethylbenzene (2.8 g, 12.3 mmol) was heated at 110° C. for 24 h. Dichloromethane was added and the resulting precipitate filtered off. The filtrate was concentrated under reduced pressure then redissolved in ethyl acetate. 10% Palladium on carbon (0.5 g, Degussa) was added and the resulting suspension hydrogenated at 5 bar for 1 h. The reaction mixture was filtered through celite, washed with ethyl acetate and, the filtrate concentrated under reduced pressure. Formic acid (10 mL) was added and the mixture heated at 110° C. for 24 h. Concentration under reduced pressure gave 7-fluoro-1-phenyl-5-trifluoromethylbenzimidazole as a purple solid (3.0 g, 87%) m/z, 281.0 (M+H)+.

Provenance & Evidence