1-(5-bromo-2-methylphenyl)ethanone

156001-51-3

74-88-4

90326-54-8

To a suspension of magnesium (1.44 g) in anhydrous ether (50 mL) was slowly added a solution of iodomethane (8.4 g) in anhydrous ether (10 mL) and the reaction mixture was stirred for 2 hours at room temperature. Subsequently, 5-bromo-2-methylbenzonitrile (4 g) was added and the reaction mixture was refluxed for 4 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution at 0 °C. Extraction was carried out by adding ethyl acetate (EtOAc). After separation of the organic phase, it was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The residue was dissolved in a mixture of ice and concentrated sulfuric acid and stirred at room temperature for 68 hours. After completion of the reaction, the organic phase was separated by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (cyclohexane/ethyl acetate, 9:1) to afford the target product 1-(5-bromo-2-methylphenyl)ethanone in 74% yield.LC-MS (Method 1): retention time (Rt) = 3.52 min.