Thionyl Chloride → 2-(2-Chloroethoxy)pyridine hydrochloride

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.55 ml, 7.55 mmol) was added to a solution of 2-(2-hydroxyethoxy)pyridine (700 mg, 5.04 mmol), (J. Org. Chem. 1977, 42, 1500), in trichloromethane (20 ml) at 5° C. The mixture was stirred for 1 hour at 5° C, allowed to warm to ambient temperature and stirred for a further 1 hour. The volatiles were removed by evaporation and by azeotroping with toluene to give 2-(2-chloroethoxy)pyridine hydrochloride (970 mg, 99%).

Provenance & Evidence