Phosphorus tribromide → 2-{2-[4-(2-Bromo-ethyl)-phenyl]-ethyl}-isoindole-1,3-dione

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Reaction Steps

A solution of 2-{2-[4-(2-Hydroxy-ethyl)-phenyl]-ethyl}-isoindole-1,3-dione (Preparation 10, 22.37 g) and phosphorus tribromide (8.20 g) in toluene (500 mL) was refluxed for 4 hours. The mixture was allowed to cool to room temperature, diluted with ethyl acetate (300 mL) and carefully quenched with sodium bisulphite/sodium bicarbonate (1:1) in water (100 mL). The organic layer was separated and washed with further sodium bisulphite/sodium bicarbonate (1:1) in water (100 mL), dried over sodium sulphate and concentrated in vacuo. The resulting solid (24.26 g) was triturated with heptane:tert-butyl methyl ether (100 mL; 9:1, by volume) to give the title compound as a pale green solid, 17.94 g.

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