Sodium Acetate → 5-Bromobenzo[b]furan-3(2H)-one

Participants

Reaction Steps

A solution of 8.34 g (33.4 mmol) of 1-(5-bromo-2-hydroxyphenyl)-2-chloroethanone and 3.3 g (40.1 mmol) of anhydrous sodium acetate in 350 ml of methanol is heated at 65° C. for one hour, subsequently evaporated to dryness, the residue is taken up in 50 ml of water, and the aqueous mixture is extracted twice with 50 ml of methylene chloride each time. After the combined organic phases have been dried over sodium sulfate and the solvent has been stripped off, the crude product is purified by column chromatography on silica gel (n-heptane/methylene chloride 7:3), giving 2.14 g of 5-bromobenzofuran-3-one as yellow solid; LC/MS: 214 (M+H).

Provenance & Evidence