Hydrochloric Acid → 1-(2-Chloro-4-methylphenyl)ethanone

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A mixture of 2-chloro-4methylbenzonitrile (2.00 g, 13.19 mmol) in toluene (25 ml), was prepared at room temperature and 3M bromo methyl magnesium (13.2 ml, 39.68 mmol) in diethylether, 3M was added dropwise and the mixture then heated to reflux (100-110° C.) for 16 h. The mixture was then cooled to 0° C. and then adjusted to pH 2 with 2M aqueous HCl. The mixture was then heated to reflux as above for 2 h. The mixture was then basified with 2M NaOH to pH 11, extracted with EtOAc (100 ml), the organic phase dried over MgSO4 and then concentrated under reduced pressure. The crude product was then purified by column chromatography (0-10% EtOAc/Hexanes) to afford 1-(2-chloro-4-methylphenyl)ethanone as a pale yellow oil (1.60 g, 9.50 mmol, 72%).

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