Hydrochloric Acid → HCID 18445393, compound

Participants

Reaction Steps

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran5-yl)-ethanone (1.69 g, 8.88 mmol) in dichloromethane (25 mL) was slowly added a suspension of AlCl3 (2.96 g, 22.2 mmol) in dichloromethane (30 mL). Bromine (1.61 g, 10.7 mmol) was added dropwise and the mixture was stirred at room temperature for 6 hours then cooled to 0° C. and aqueous HCl (1N) was added and the mixture extracted with dichloromethane, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: EtOAc/10:1 to 2:1) to give 1.94 g 1-(7-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran5-yl)-ethanone (81%). 1H NMR (300 MHz, CDCl3, ppm): δ: 1.39 (s, 6H), 2.56 (s, 3H), 4.37 (s, 2H), 7.69 (d, J=1.76 Hz, 1H), 7.95 (d, J=1.76 Hz, 1H).

Provenance & Evidence