Benzoyl Peroxide → 7-Bromo-5-[(4-methylphenyl)sulfonyl]-1-benzofuran

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-5-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1-benzofuran (353 mg, 1 mmol; Intermediate 78), NBS (178 mg, 1 mmol) and dibenzoylperoxide (24 mg, 0.1 mmol) in carbon tetrachloride (20 mL) was heated to 80° C. for 2 h. TEA (2 mL) was added and the mixture was heated for another 2 h. Flash chromatography using EtOAc/hexane 10:90→25:75 as eluent gave the title product as a white crystalline material. Yield: 130 mg (37%). 1H NMR (400 MHz, CDCl3) δ 2.39 (s, 3H), 6.93 (d, 1H), 7.30 (d, 2H), 7.78 (d, 1H), 7.84 (d, 2H), 8.02 (d, 1H), 8.19 (d, 1H).

Provenance & Evidence