Azobisisobutyronitrile → 6-(Bromomethyl)pyridine-3-carbonitrile

Participants

Reaction Steps

To a solution of 6-Methylnicotinonitrile (11-1) (Lancaster) (15 g, 127 mmol) in carbon tetrachloride (300 ml) was added N-bromosuccinimide (27.12 g, 152.4 mmol). The resulting solution was degassed and purged with nitrogen and AIBN (2,2′-azobisisobutyronitrile) (2.08 g, 12.6 mmol) was added. After 7 hours at 85° C., another batch of AIBN (1.04 g) was added and stirring was continued for another hour. After removal of the solvent the crude product was subjected to flash column chromatography in ethylacetate/hexanes to yield 10 g pure material (40%).

Provenance & Evidence