Thionyl Chloride → 3-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine

Participants

Reaction Steps

To a suspension of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (26.7 g; 100 mmol; example 5 e]) in dichloromethane (100 ml), was added at 0° C. 10.9 ml (150 mmol) of thionyl chloride within 0.5 hours. Stirring was continued at ambient temperature for 1 hour. Afterwards, ice water was added and the mixture was stirred vigorously. Then, the layers were separated, the aqueous phase was extracted with 100 ml of dichloromethane. The combined organic phases were washed with water, aqueous sodium hydrogen carbonate, brine, and dried with anhydrous sodium sulfate. After evaporation, 27.9 g (97.6%) of 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine were obtained as a light brown solid.

Provenance & Evidence