Potassium Phosphate, Dibasic → 7-(4-Methoxyphenyl)-benzofuran-5-carbaldehyde

Participants

Reaction Steps

To a solution of 7-(4-methoxyphenyl)-5-methyl-benzofuran (4.66 g, 19.58 mmol) in carbon tetrachloride (560 ml) was added NBS (3.83 g, 21.54 mmol) and AIBN (75 mg). The solution was brought to reflux for 4 h, cooled to room temperature, reduced by half, and the solids were filtered off. The solution was then concentrated to a yellow solid and anhydrous CH3CN (230 ml) was added. Then potassium benzeneselenite (5.34 g, 23.5 mmol), and K2HPO4 (4.09 g, 23.48 mmol) were added and then reaction was refluxed for 1.5 h after which it was allowed to cool to room temperature. The solution was then passed through a silica plug and concentrated under high vacuum. Chromatography (100% CH2Cl2) afforded 3.3 g (67%) product as a light orange solid: mp 79–80° C.; 1H NMR (300 MHz, DMSO-d6): δ 3.85 (3H, s), 7.13 (2H, d, J=8.8 Hz), 7.23 (1H, d, J=2.2 Hz), 7.88 (2H, d, J=8.8 Hz), 8.02 (1H, d, J=1.4 Hz), 8.23 (2H, m), 10.13 (1H, s); MS (ESI) m/z 253 ([M+H]+).

Provenance & Evidence