Thionyl Chloride → 2-Chloro-4-(chloromethyl)pyridine

Participants

Reaction Steps

SOCl2 (4.2 g, 35.5 mol) was added dropwise to a suspension of the alcohol (5 g, 34.8 mmol) in CH2Cl2 (50 mL) at −5° C. with stirring. The mixture was stirred at room temperature overnight, then quenched with water (100 mL), and extracted with CH2Cl2 (3×100 mL). The organic layers were combined, washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/5) and afforded the title compound (5.5 g, near quantitative yield) as an oil.

Provenance & Evidence