Phosphorus tribromide → 5-(2-Bromoethyl)-2,3-dihydro-1-benzofuran

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Reaction Steps

Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g) (see Preparation 5) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10% aqueous sodium carbonate solution (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulphate and evaporated to give the title compound as an oil which crystallised on standing, yield 0.584 g, m.p. 60°-62° C.

Provenance & Evidence