Azobisisobutyronitrile → tert-butyl 2-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

Participants

Reaction Steps

NBS (8.43 g, 47.4 mmol) and AIBN (2.1 g, 12.8 mmol) were added to a solution of 1-BOC-2-methylbenzimidazole (10.0 g, 43.1 mmol) in CCl4 (120 mL) at reflux. After 21 h, the reaction was cooled and filtered. The filtrate was concentrated, and the resulting brown oil was chromatographed (silica gel, 15% EtOAc/hexanes) to afford the title compound: 1H NMR (400 MHz, CDCl3) δ 7.94-8.01 (m, 1 H), 7.70-7.75 (m, 1 H), 7.31-7.44 (m, 2 H), 4.96 (s, 2 H), 1.75 (s, 9 H),

Provenance & Evidence