Thionyl Chloride → 2-Chloro-6-(chloromethyl)pyridine

Participants

Reaction Steps

Thionyl chloride (12.6 mL; 173 mmol) in 100 mL chloroform was added dropwise to a solution of 6-chloro-2-hydroxymethylpyridine (13.0 g; 90.5 mmol), prepared as in step 3, in 100 mL chloroform. Upon complete addition the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled to ambient temperature and carefully poured into 250 mL saturated aqueous sodium bicarbonate. The layers were separated and the aqueous was extracted with dichloromethane. The extracts were dried over magnesium sulfate and concentrated. 6-chloro-2-chloromethylpyridine was isolated as a pale yellow solid by flash chromatography (20% diethyl ether in hexane).

Provenance & Evidence