Ammonium Chloride → 2-(2-Chloropyridin-4-yl)-1-(3-methoxy-5-methylphenyl)ethanone

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To a solution of methyl 3-methoxy-5-methylbenzoate (9.0 g, 50 mmol) and 2-chloro-4-methylpyridine (7.0 g, 55 mmol) in tetrahydrofuran (90 mL) was dropwise added lithium hexamethyldisilazide (75 mL, 75 mmol, 1M In THF) at 0° C. under a nitrogen atmosphere, and stirred at room temperature for 18 hours. After completion of the nucleophilic attack reaction, the reaction mixture was neutralized with a saturated ammonium chloride solution (150 mL) and extracted with ethyl acetate (300 mL×2). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated by vacuum distillation, and the concentrate (9.92 g, 72%) was used in the next reaction without further purification.

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