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

Participants

Reaction Conditions

Reaction Steps

Dissolve 6-methyl-nicotinonitrile (2 g, 17 mmol) and NBS (3.01 g, 17 mmol) in anhydrous DCE (56 mL) under nitrogen. Add AIBN (277 mg, 1.7 mmol) and heat the mixture at 80° C. for 1.5-2 h. Add another batch of AIBN (277 mg, 1.7 mmol) and heat the mixture at 80° C. for a further 1-2 h. Then add a third batch of AIBN (277 mg, 1.7 mmol) and heat the mixture at 80° C. for a further 1-2 h. Cool the reaction to room temperature and concentrate in vacuo. Dissolve the residue in DCM, add silica gel and concentrate in vacuo. Purify by chromatography on silica gel (120 g, pre-packed cartridge) eluting with cyclohexane/EtOAc (98:2 to 7:3 gradient over 55 min, 40 mL/min) to isolate the desired intermediate (2 g, 60%) as a white solid that turns red on standing at room temperature. MS (ES+) m/z: 199 (M+2)+.

Provenance & Evidence