Phosphorus tribromide → 1-Bromo-4-(1-bromoethyl)benzene

関与物質

反応手順

A solution of 1-(4-bromophenyl)ethanol (1.492 mmol) in dichloromethane (8 mL) at 0° C. was treated dropwise with a solution of phosphorous tribromide (0.597 mmol) in dichloromethane (2 mL). The reaction was allowed to warm to room temperature and was stirred overnight. The reaction was then quenched with saturated aq sodium bicarbonate (10 mL) and was stirred for 2 h. The biphasic mixture was further diluted with dichloromethane (50 mL) and the organic layer was separated from the aqueous layer. The organic layer was dried over sodium sulfate, filtered and concentrated to dryness in vacuo. Purification of the residue by flash chromatography (0-25% ethyl acetate/hexanes) gave the title product (91 mg, 23% yield) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.97 (d, J=6.82 Hz, 3 H) 5.50 (q, J=6.82 Hz, 1 H) 7.48 (d, J=8.59 Hz, 2 H) 7.57 (m, J=8.59 Hz, 2 H).

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