Thionyl Chloride → 3-Chloro-5-(chloromethyl)-2-pyridinecarbonitrile

Participants

Reaction Steps

To a stirred solution of 3-chloro-5-(hydroxymethyl)picolinonitrile (from the previous step) in CH2Cl2 (0.2 M) at 0° C. was added thionyl chloride (10 eq). After stirring at room temperature overnight the reaction mixture was concentrated under vacuum and the resulting crude was purified by chromatography (silica gel, 20-50% EtOAc in hexanes) to afford 3-chloro-5-(chloromethyl)picolinonitrile as a colorless oil.

Provenance & Evidence