Thionyl Chloride → 2-(3-(Chloromethyl)phenoxy)-3-methylpyridine

Participants

Reaction Steps

(3-(3-Methylpyridin-2-yloxy)phenyl)methanol from Step 1 (3.3 g, 15 mmol), in dichloromethane (50 mL), was cooled to 0° C., and treated dropwise with thionyl chloride (1.34 mL, 18.4 mmol). The reaction mixture was allowed to warm to ambient temperature and was stirred for 3 h. Saturated aqueous sodium bicarbonate (20 mL) was added and the mixture was stirred at RT for 5 min. The organic layer was separated, dried over sodium sulfate, filtered and concentrated by evaporation to afford the title compound (3.6 g, 99% yield) as an oil.

Provenance & Evidence