Azobisisobutyronitrile → 3-(Bromomethyl)-1-benzothiophene

Participants

Reaction Steps

3-Methylbenzo[b]thiophene (9.9 g, 67 mmol) is heated in carbon tetrachloride (133 ml) to near reflux in the presence of n-bromosuccinimide (11.9 g, 67 mmol, 1.0 eq.). 2,2′Azobisisobutyronitrile (2.2 g, 13.3 mmol, 0.2 eq.) is added and the resulting mixture is refluxed for two hours. After cooling, the reaction mixture is filtered through a glass-fritted funnel, and the filtrate is concentrated. The residue is triturated with petroleum ether and toluene to afford 6.42 g of 3-Bromomethylbenzo[b]thiophene (42%). The title amine is prepared from 3-(bromomethyl)-benzo[B]thiophene in a similar fashion as described in U.S. Pat. No. 4,321,398.

Provenance & Evidence