Phosphorus tribromide → 5-(2-bromoethyl)-2,3-dihydro-1H-indene

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Reaction Steps

Phosphorus tribromide (3.5 ml) was added dropwise to a solution of 5-(2-hydroxyethyl)indane (14.0 g) (FR-A-2139628) in carbon tetrachloride (100 ml). The mixture was stirred at room temperature for 0.5 hour and then heated under reflux for 2 hours. Ice (100 g) was added and the mixture partitioned between dichloromethane and 10% aqueous sodium carbonate solution. The layers were separated and the aqueous layer extracted twice with dichloromethane. The combined dichloromethane extracts were dried (MgSO4) and evaporated to give an oil which was purified by column chromatography on silica using dichloromethane as the eluant. Appropriate fractions were combined and concentrated in vacuo to give the title compound as a colourless oil, yield 10.5 g.

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