5-Bromo-1-indanone → 5-bromo-2,3-dihydro-1H-inden-1-ol

Participants

Reaction Steps

To a solution of 5-bromo-2,3-dihydroinden-1-one (1.1 g, 5.2 mmol) in ethanol (100 mL) was added sodium borohydride (218 mg, 5.7 mmol). The mixture was stirred at room temperature for 24 hours. Then the resultant mixture was filtered. The filtrate was acidified with hydrochloric acid aqueous solution (1N) and the solvent was removed in vacuo. The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined organic phase was dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1) to give 5-bromo-2,3-dihydro-1H-inden-1-ol (1 g, 90%) as a yellow oil. LRMS (M+H+) m/z: calcd 211.98. found 211. 1H NMR (300 MHz, CDCl3): δ 7.40 (s, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.27 (d, J=7.8 Hz, 1H), 5.22-5.18 (m, 1H), 3.09-2.99 (m, 1H), 2.86-2.76 (m, 1H), 2.55-2.46 (m, 1H), 2.01-1.76 (m, 1H), 1.75 (s, 1H).

Provenance & Evidence