Hydrogen Bromide → 6-chloro-2,3-dihydro-1H-inden-4-ol

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Reaction Conditions

Reaction Steps

To 6-chloro-4-methoxyindane (12.0 g, 0.072 mol) was added hydrogen bromide (30 wt. % in acetic acid, 325 mL) and the reaction mixture was stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (750 mL), washed with water (3×500 mL), saturated aqueous sodium bicarbonate (2×500 m/L), saturated aqueous sodium chloride (500 mL), dried (sodium sulfate) and the solvent was removed in vacuo to provide a brown oil. Purification by flash column chromatography (silica, dichloromethane) provided 10.5 g (80%) of 6-chloroindan-4-ol as a pale yellow solid. mp 56-59° C.; Anal. calcd. for C9H9ClO.0.2H2O: C, 62.77; H, 5.50. Found: C, 62.75; H, 5.26.

Provenance & Evidence