Acetyl chloride → 2-Acetylbenzo[b]thiophen-4-yl benzoate

Beteiligte Stoffe

Reaktionsschritte

A solution of acetyl chloride (0.25 ml) in dichloromethane (1.5 ml) was added dropwise under nitrogen at ambient temperature to a stirred suspension of anhydrous aluminium chloride (0.94 g) in dichloromethane (10 ml) and the mixture was stirred at ambient temperature for 15 minutes. A solution of benzo[b]thiophen-4-yl benzoate (0.6 g) in dichloromethane (4 ml) was added, the mixture was stirred at ambient temperature for 18 hours, then it was poured onto ice-water (60 ml). The product was extracted into dichloromethane (2×50 ml), the combined extracts were washed with water (50 ml), saturated aqueous sodium hydrogencarbonate solution (20 ml), water (2×50 ml) and saturated aqueous sodium chloride solution (40 ml), then they were dried (MgSO4) and the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using a 7:3 mixture of dichloromethane and petroleum ether (b.p. 60-80° C.) as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 2-acetylbenzo[b]thiophen-4-yl benzoate (0.13 g) as a cream solid which was used without further purification.

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