Thionyl Chloride → 2-(Chloromethyl)-5-methylpyridine hydrochloride

Participants

Reaction Steps

To (5-methyl-pyridin-2-yl)-methanol (310 g) in dichloromethane (1.2 L) was added thionyl chloride (200 mL) dropwise over 1.5 hours. The reaction was stirred for 2 hours, and then concentrated under vacuum. Ethyl acetate (1 L) was added, and the mixture was again concentrated to dryness. Additional ethyl acetate (1.5 L) was added, and the suspension was stirred for 30 minutes and then filtered to isolate the desired product as a solid, which was dried under nitrogen.

Provenance & Evidence