1,2-Dimethoxyethane → 3-Hydroxy-6-fluoro-1-indanone

A mixture of 3-bromo-6-fluoro-1-indanone (2.50 g, 10.0 mmoles) and silver carbonate (4.19 g, 15.2 mmoles, Aldrich) in dimethoxyethane (85 mL) and water (65 mL) was stirred overnight at ambient temperature. The mixture was filtered through a pad of celite, and the filtrate was diluted with water (500 mL) and extracted with ethyl acetate (4×100 mL). The combined extracts were washed with water (100 mL) and brine (75 mL), dried over sodium sulfate, filtered, and evaporated in vacuo to give 2.80 g (quantitative) of crude 3-hydroxy-6-fluoro-1-indanone which was used without further purification. Chromatography of 0.41 g on silica gel, eluting with hexane:ethyl acetate (3:4) gave 0.050 g of analytically pure 3-hydroxy-6-fluoro-1-indanone as a tan solid, mp 73-76° C.;