HCID 21071776, compound → 7-Bromo-5-methyl-1-benzofuran

Participants

Reaction Steps

To a 2 L round bottom flask was added PPA (3 g), anhydrous chlorobenzene (1.0 L) and the mixture was brought to reflux followed by the slow addition of 2-bromo-1-(2,2-dimethyoxy-ethoxy)-4-methyl benzene (22.9 g, 83.3 mmol) in chlorobenzene (200 ml) by addition funnel over a 2 h period. The reaction was then cooled and passed through a silica plug (washed with chlorobenzene) and concentrated to a mixture of product plus 4-iodo-2-methylphenol. Column chromatography (10% EtOAc/hexane) afforded 11.54 g (66%) of product as a clear oil: 1H NMR (300 MHz, DMSO-d6): δ 2.40 (3H, s), 7.02 (1H, d, J=2.2 Hz), 7.39 (1H, s), 7.45 (1H, s), 8.07 (1H, d, J=2.2 Hz).

Provenance & Evidence