N-bromobutanimide → 5-Benzofuranacetic acid

Participants

Reaction Steps

To the solution of (2,3-dihydro-benzofuran-5-yl)-acetic acid (0.89 g, 5 mmol) and N-bromosuccinimide (0.89 g, 5 mmol) in carbon tetrachloride (10 mL) was added 10 mg of benzoyl peroxide. The mixture was refluxed for 3 h and cooled with ice. The solid was removed by filtration, the filtrate was concentrated, the residue was crystallized from 1:1 ethyl acetate:hexane to give a white solid (390 mg, 44%). 1H NMR (400 MHz, CDCl3) δ 10.5 (b s, 1H), 7.62 (d, J=2.2 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.21 (dd, J=8.4, 1.8 Hz, 1H), 6.74 (d, J=2.2 Hz, 1H), 3.75 (s, 2H).

Provenance & Evidence