Thionyl Chloride → 3-[(6-Bromopyridin-2-yl)(chloro)methyl]benzonitrile

Participants

Reaction Steps

To a mixture of 3-[(6-bromopyridin-2-yl)(hydroxy)methyl]benzonitrile (4.88 g, 16.88 mmol) in CH2Cl2 (60 mL) @ 0° C. under N2 was added SOCl2 (2.01 mL, 16.88 mmol). The mixture was warmed to rt and stirred for 48 hr. The mixture was cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate and extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (25-50% CH2Cl2 in Hexanes) to give 3-[(6-bromopyridin-2-yl)(chloro)methyl]benzonitrile. LRMS m/z (M+H) Calcd.: 307.0, found: 307.0.

Provenance & Evidence