Thionyl Chloride → 2-(3-(Chloromethyl)phenoxy)-5-methylpyridine

Participants

Reaction Steps

(3-(5-Methylpyridin-2-yloxy)phenyl)methanol from Step 1 (1.9 g, 8.8 mmol), in dichloromethane (25 mL), was cooled to 0° C., and treated dropwise with thionyl chloride (0.773 mL, 10.6 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 (2.1 g, 99% yield) as an oil.

Provenance & Evidence