HCID 70284941, compound → 1-(5-Chloro-1-benzothiophen-3-yl)ethan-1-one

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Reaction Steps

A mixture of 1-(5-chloro-2,3-dihydrobenzo[b]thiophen-3-yl)-2-phenoxyethanone (15.3 g), acetic acid (75 ml) and concentrated sulphuric acid (15 drops) was heated at 90°-95° C. under nitrogen for 20 hours, then the solvent was removed in vacuo. The residue was partitioned between dichloromethane (250 ml) and 5M aqueous sodium hydroxide solution (100 ml), then the aqueous phase was separated and washed with dichloromethane (50 ml). The combined dichloromethane solutions were washed with water (100 ml), dried (MgSO4), and the solvent removed in vacuo to leave 3-acetyl-5-chlorobenzo[b]thiophen as a red-brown oil (10.7 g) which solidified slowly at ambient temperature.

Provenance & Evidence