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

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.

1. stirringthe mixture was stirred at ambient temperature for 18 hours
2. additionit was poured onto ice-water (60 ml)
3. extractionThe product was extracted into dichloromethane (2×50 ml)
4. washthe 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)
5. dry with materialthey were dried (MgSO4)
6. customthe solvent was removed in vacuo
7. customThe residue was purified by flash chromatography over silica using
8. additiona 7:3 mixture of dichloromethane and petroleum ether (b.p. 60-80° C.) as eluant
9. customthe solvents removed in vacuo

ORD record

ord-023d6e76122244babccdf22bf008ac50

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900216B2