N-bromobutanimide → HCID 19347979, compound

Participants

Reaction Steps

Catalytic azobisisobutylnitrile (AIBN, 0.28 g) and N-bromosuccinimide (4.8 g, 26.8 mmol) were added to a solution of ethyl 3-chloro-6-methylbenzo[b]thiophene-2-carboxylate (Preparation 9, 6.5 g, 25.5 mmol) in tetrachloromethane (50 ml), under a nitrogen atmosphere. The mixture was heated to reflux for 5 hours, cooled, and then loaded onto a silica gel column. The product was eluted with a gradient mixture of dichloromethane and hexane (initially 30:70 increasing to 50:50, and then 70:30). The solvent was removed under reduced pressure to leave the title compound as a colourless solid (8.7 g)

Provenance & Evidence