Chlorosuccinimide → 2-(4-(Chloromethyl)phenyl)pyridine

Participants

Reaction Steps

To a solution of 2-(p-tolyl)pyridine (1.7 g) and N-chlorosuccinimide (1.5 g) in carbon tetrachloride (30 mL) was added α,α-azobisisobutyronitrile (0.033 g), and the mixture was heated under reflux for 5 hours. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1-3/1) to give 4-(pyridin-2-yl)benzyl chloride (1.1 g).

Provenance & Evidence