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

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Reaction Steps

Phenyltrimethylammonium tribromide (1.46 g, 3.90 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)ethanone (2) (1.04 g, 3.82 mmol) in anhydrous THF (15 mL) in three portions. The reaction mixture was stirred at rt for 12 h. Then an aqueous sodium bicarbonate solution (5%, 10 mL) and an aqueous sodium thiosulfate solution (10%, 5 mL) were added. The mixture was extracted with dichloromethane, and combined organics were concentrated by rotary evaporation. The resulting residue was purified by Biotage silica gel column chromatography eluting with dichloromethane to give bromo ketone 3 as a white solid (1.08 g, 81% yield): 1H NMR (500 MHz, CDCl3) δ 4.49 (s, 3H), 5.35 (s, 2H), 7.21 (d, 1H), 7.40 (m, 5H), 8.15 (dd, 1H), 8.49 (d, 1H).

Provenance & Evidence