Azobisisobutyronitrile → 4-(Bromomethyl)-3-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

14.7 g (0.1 mol) of 3-methoxy-4-methylbenzonitrile were dissolved in 210 ml of 1,2-dichloroethane, brominated with 19.1 g (0.11 mol) of NBS in portions over the course of 1 h in the presence of catalytic amounts of azobisisobutyronitrile at 82° C. and, after the addition was complete, stirred at 82° C. for a further 30 min. After addition of n-heptane, precipitated succinimide was removed, and the solvent was stripped off. The yield was 18.5 [lacuna] (82%). 1H-NMR (DMSO-d6 ; δ in ppm): 7.60 (dd, 1H); 7.50 (d, 1H); 7.40 (dd, 1H); 4.68 (s, 2H); 3.96 (s, 3H)

Provenance & Evidence