Allyl bromide → 1-(3-Bromopropyl)-3-chlorobenzene

Participants

Reaction Steps

A solution of 3-(3-chloro-phenyl)-propan-1-ol (12.54 g, 73.6 mmol) and N,N′-carbonyl diimidazole (13.12 g, 81 mmol) in CH3CN was stirred at room temperature for 1 h. Allyl bromide (53.43 g, 442 mmol) was added and the reaction was heated at reflux for 24 h. The reaction was cooled to room temperature and brine and EtOAc were added. The aqueous solution was extracted with EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography provided the title compound in about 85% yield. 1H NMR (400 MHz, CDCl3) δ 7.30–7.09 (m, 4H), 3.38 (t, 2H), 2.76 (t, 2H), 2.15 (t, 2H).

Provenance & Evidence