Water → 5-Fluoro-3-methylbenzofuran

Participants

Reaction Conditions

Reaction Steps

(2-Acetyl-4-fluoro-phenoxy)-acetic acid (1.87 gm, 8.8 mmol) is dissolved in acetic anhydride (60 mL) and treated with sodium acetate (10 gm, 0.12 mol). The resulting mixture is heated to 110° C. for 5 hr, then cooled to 0° C. H2O (100 mL) is added and the solution is stirred overnight at room temperature. The aqueous solution is then extracted into Et2O (2×75 mL). The combined organic extracts are washed with 3% aqueous KOH (2×75 mL), H2O (2×75 mL) and brine (1×75 mL), then dried over Na2SO4, filtered and concentrated. The crude product is purified by chromatography using hexane to give the title compound (1.07 gm, 81% yield).

Provenance & Evidence