N-bromobutanimide → 5-Benzofuranacetic acid

Participants

Reaction Steps

N-bromosuccinimide (0.89 g, 5.0 mmol) was added to a solution of 2,3-dihydrobenzofuran-5-ylacetic acid (0.89 g, 5.0 mmol) and benzoyl peroxide (10 mg) in carbon tetrachloride (100 mL) and refluxed for 3 hours. The mixture was cooled to room temperature, filtered and concentrated. The product was recrystallized from ethyl acetate:hexane (2:1) to give a 0.39 g (44%) of white solid. 1H NMR (CD3OD) δ 7.62 (1H, d, J=2.4 Hz), 7.52 (1H, d, J=0.8 Hz), 7.46 (1H, d, J=8.4 Hz), 7.21 (1H, dd, J=1.6, 8.4 Hz), 6.74 (1H, d, J=3.2 Hz), 3.74 (2H, s).

Provenance & Evidence