Dimethylformamide → 2-Bromo-5-[chloro(2,3,6-trifluorophenyl)methyl]-4-methylpyridine

Participants

Reaction Steps

To a solution of (6-bromo-4-methylpyridin-3-yl)(2,3,6-trifluorophenyl)methanol (4.60 g, 13.9 mmol) in methylene chloride (70 ml), thionyl chloride (10.1 ml, 139 mmol) and N,N-dimethylformamide (0.60 ml) were added at 0° C., and the resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the resulting residue, and subsequently water and then saturated aqueous sodium hydrogencarbonate were added thereto at 0° C. After the organic layer was separated, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was concentrated under reduced pressure, to obtain the title compound (4.65 g, 13.3 mmol, 96%) as a pale brown solid.

Provenance & Evidence