Azobisisobutyronitrile → 3'-Bromo-4'-(bromomethyl)biphenyl-2-carbonitrile

Participants

Reaction Steps

A solution of 1.0 g (3.7 mmol) of 3'-bromo-4'methyl-1,1'-biphenyl-2-nitrile (Step C) in 15 mL of carbon tetrachloride under a nitrogen atmosphere was treated with 0.720 g (4.04 mmol) of N-bromosuccinimide followed by 60 mg (0.37 mmol) of azobisisobutyronitrile (AIBN). The reaction mixture was heated at reflux for four hours, cooled to room temperature and filtered through Celite. The solvent was removed under vacuum and the residue was dissolved in methylene chloride and treated with decolorizing carbon. The solids were filtered through Celite and the solvent removed under vacuum. The resulting solid was triturated with cold ether, filtered and air dried to afford 920 mg (71%) of the product as an off-white solid. 1H NMR (200 MHz, CDCl3): δ 4.64 (s, 2H), 7.4-7.8 (m, 7H). EI-MS: calculated for C14H9Br2N 351; found 351 (M+, 20%); 271 (M-Br, 100%).

Provenance & Evidence