Hexane → 5-Bromo-6-methyl-1-benzofuran

Participants

Reaction Steps

Part E. A solution of the above compound (780 mg) and N-bromosuccinimide (1.24 g, 6.97 mmol) in dichloroethane (10 mL) was heated to reflux overnight, then cooled, filtered and evaporated. Column chromatography (hexane, then 2:98 ethyl acetate-hexane) gave first 5-bromo-6-methylbenzofuran (270 mg, 1.27 mmol, 22%), then 5-bromo-6-methyl-2,3-dihydrobenzofuran (923 mg, 4.33 mol, 75%), both as solids. For the dihydro product: TLC RF 0.35 (2:98 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3): d 7.31 (1H, s), 6.68 (1H, s), 4.56 (2H, t, J=8.8 Hz), 3.17 (2H, t, J=8.8 Hz), 2.33 (3H, s). MS (H2O-GC/MS): m/e 215 (76), 213 (100).

Provenance & Evidence