1-(3-Nitro-4-phenylmethoxyphenyl)ethanone → 2-Bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanone

Participants

Reaction Steps

Phenyltrimethylammonium tribromide (109.00 g, 290.00 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)ethanone (2) (65.60 g, 242.00 mmol) in anhydrous THF (600 mL) in three portions, and the reaction mixture was stirred at rt for 12 h. The solids were then collected by filtration and the filtrate concentrated. The product was precipitated from chloroform upon the addition of hexanes, then collected by filtration and dried under vacuum to give bromo ketone 3 as a light yellow solid (63.33 g, 75% yield): 1H NMR (500 MHz, CDCl3) δ 4.37 (s, 3H), 5.35 (s, 2H), 7.21 (d, 1H), 7.40 (m, 5H), 8.15 (dd, 1H), 8.49 (d, 1H).

Provenance & Evidence