Thionyl Chloride → 5-Bromo-2-(chloromethyl)pyridine hydrochloride

Participants

Reaction Steps

A mixture of (5-bromo-pyridin-2-yl)-methanol (104 g, 0.66 mol) in methylene chloride (833 mL) in two neck flask was placed in water bath. Thionyl chloride (80.5 mL, 1.33 mol) was dropwise added to the reaction mixture using dropping funnel and stirred at room temperature for 1.5 hr. Then, thionyl chloride (20 mL, 0.33 mol) was additionally added to the reaction mixture and stirred for 2.5 hr. After completion of the reaction, the reaction mixture was transferred to a round bottom flask. Methylene chloride and thionyl chloride were evaporated off. Toluene (2×100 mL) was added to the residue and azeotropically removed all the residual thionyl chloride. The residue was dried on vacuum for overnight to give the title compound (129.6 g, 96%) as a pink solid. MS-ESI m/z 207.91 (M+H)+.

Provenance & Evidence