Azobisisobutyronitrile → Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate

Participants

Reaction Steps

3-Chloro-4-methyl-2-thiophenecarboxylic acid methyl ester (3.81 g) was dissolved in carbon tetrachloride (40 mL). To the solution, N-bromosuccinimide (3.56 g) and α,α′-azobisisobutyronitrile (200 mg) were added, and the mixture was heated under reflux for 2.5 hours. The insoluble material was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate hexane=1:19→1:9), to thereby give the title compound (2.92 g) as a yellow oil.

Provenance & Evidence