Methanol → Methyl 4-bromocinnamate

Participants

Reaction Steps

To a stirred solution of (2E)-3-(4-bromophenyl)prop-2-enoic acid (4.5 g, 0.020 mol) in MeOH (20 mL), sulfuryl dichloride (2.7 g, 0.023 mol) was added dropwise at 0° C. The resulting solution was heated to reflux for 1 h. The reaction mixture was allowed to cool to rt and concentrated to dryness under reduced pressure to yield a residue, which was subjected to flash column chromatography on silica gel (5-10% EtOAc/petroleum ether) to afford compound 66c as a colorless oil. Mass Spectrum (GCMS, ESI pos.): Calcd. for C10H9BrO2: 241.1 (M). found: 241.0.

Provenance & Evidence