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

Participants

Reaction Steps

A mixture of 70.3 g of 2-chloro-5-(hydroxymethyl) pyridine and 50 ml of 1,2-dichloroethane was dropwise added to a mixture of 87.4 g of thionyl chloride and 100 ml of 1,2-dichloroethane during 30 minutes in a water bath of 5°-20° C. The mixture was stirred for an hour and a half at room temperature and for 4 hours and a half under refluxing. After concentrating, to the residue were added 200 ml of chloroform and 60 ml of water and then added portionwise 20 g of sodium hydrogen carbonate under stirring. The organic phase was separated, treated with active carbon and concentrated to obtain 75.9 g of 2-chloro-5-(chloromethyl)pyridine as a yellowish brown solid.

Provenance & Evidence