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 a 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) δ7.30-7.09 (m, 4H), 3.38 (t, 2H), 2.76 (t, 2H), 2.15 (t, 2H).

Provenance & Evidence