Azobisisobutyronitrile → Ethyl-4-bromo-3-methyl-but-2-enoate (E/Z; 55/45)

Participants

Reaction Steps

To ethyl 3-methyl-2-butenoate (10.0 g, 78.0 mmol) in 80 ml of carbon tetrachloride heated under gentle reflux is added N-bromosuccinimide (15.0 g, 84.0 mmol) in portions, followed by traces of radical initiator (benzoyl peroxide, ca. 0.2 g, and AIBN, ca. 0.1 g) in portions over one hour. After the final addition, the mixture is heated under reflux for 30 min. The reaction mixture is cooled and filtered and the solvent is removed by rotoevaporation to give ethyl 4-bromo-3-methyl-2-butenoate.

Provenance & Evidence