Carbon Tetrachloride → 2-(Chloromethyl)quinoline

Participants

Reaction Steps

2-Methylquinoline (5.0 g) was dissolved in carbon tetrachloride (25 mL), imide N-bromosuccinate (6.2 g) and 2,2′-azobisisobutyronitrile (AIBN) (57 mg) were added thereto, and the mixture was refluxed for 4 hr. After ice-cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1) to give the title compound (3.7 g) as a pale-yellow solid.

Provenance & Evidence