Iodine → 2-(Iodomethyl)-2,3-dihydro-1-benzofuran

Participants

Reaction Steps

To a solution of 2-allylphenol (10 g, 75 mmol) in dichloromethane (150 ml) was added SnCl4 (29.7 g, 37.3 mmol, 0.5 eq) and iodine (19 g, 75 mmol, 1 eq) at room temperature. After stirring for 5.5 hours, the reaction mixture was diluted with additional dichloromethane (200 ml) and then quenched with water (200 ml). The organic layer was separated and the aqueous layer was adjusted pH to ˜8 with sodium bicarbonate and then extracted with dichloromethane (3×150 ml). The organic layers were combined, washed with 5% aqueous Na2S2O4 (200 ml), dried over anhydrous magnesium sulfate, filtered, and then concentrated under vacuum. The crude material was purified by silica gel chromatography using with 0.5-1% ethyl acetate in petroleum ether to elute. The product-containing fractions were combined and concentrated to afford 2-(iodomethyl)-2,3-dihydro-1-benzofuran as brown oil (7 g, 36%); 1H NMR (300 MHz, CDCl3): δ 7.09-7.17 (m, 2H), 6.74-6.89 (m, 2H), 4.84-4.93 (m, 1H), 3.30-3.47 (m, 3H), 3.00-3.08 (m, 1H).

Provenance & Evidence