Methanol → 1-Chloro-2-fluoro-4-methoxy-5-nitrobenzene

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To a mixture of potassium tert-butoxide (3.0 g, 26.9 mmol) in DMF (20 mL), methanol (0.79 g, 24.8 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes then a solution of 1-chloro-2,4-difluoro-5-nitrobenzene (4.0 g, 20.7 mmol) in DMF (20 mL) was added at 0° C. and the reaction mass stirred for 3 hours at room temperature. Water (200 mL) was added to the reaction mixture and reaction mass was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (80 mL), brine (80 mL), dried (Na2SO4) and concentrated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 20-25% EtOAc in hexane to give the desired product (3 g, 71%) as a solid.

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