Thionyl Chloride → 2-Chloro-5-(chloromethyl)pyridine

Participants

Reaction Steps

On a water bath at 5°-20° C., a mixture of 70.3 g of 2-chloro-5-(hydroxymethyl)pyridine and 50 ml of 1,2-dichloroethane was added dropwise to a mixture of 87.4 g of thionyl chloride and 100 ml of 1,2-dichloroethane over a period of 30 minutes. The whole mixture was stirred at room temperature for 90 minutes and, then, under reflux for 4.5 hours. The reaction mixture was then concentrated and the residue was diluted with 200 ml of chloroform and 60 ml of water. Then, with stirring, 20 g of sodium hydrogen carbonate was added in small portions. Thereafter, the organic layer was separated, treated with activated carbon and concentrated to give 75.9 g of 2-chloro-5-(chloromethyl)pyridine as a yellow brown solid.

Provenance & Evidence