Azobisisobutyronitrile → 5-Bromo-2-(bromomethyl)benzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

According to the procedure of S. Gronowitz, et al., Synth. Commin., 6, (7), 475 (1976), to a stirred, boiling partial solution of N-bromosuccinimide (17.63 g, 0.099 mol) in CCl4 (200 mL) was added 2,2'-azobis-(2-methylpropionitrile) (1.1 g, 0.007 mol). After one minute, a solution of 5-bromo-2-methylbenzthiophene (15.0 g, 0.066 mol) in CCl4 (100 mL) was added. The resulting mixture was heated at reflux for 2 hours and cooled to 0° C. The solid was filtered. The filtrate was concentrated to give 18.19 g (90%) of product as an orange solid.

Provenance & Evidence