Chlorodifluoromethane → 4-(Difluoromethoxy)-2-fluoro-1-nitrobenzene

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N,N-Dimethylformamide (15 mL) was added to 3-fluoro-4-nitrophenol (1.01 g, 6.43 mmol) and potassium carbonate (5.33 g, 38.6 mmol) in a 50 mL stainless steel reactor. The vessel was sparged briefly with CF2HCl, chilled with dry ice, and then chlorodifluoromethane (3.34 g, 38.6 mmol) was transferred into the reactor through a polypropylene tube. The mixture was stirred at 85° C. for 2 hours. The supernatant mixture was concentrated onto silica gel. Purification via flash chromatography (0-40% ethyl acetate/hexanes) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.28 (t, J=9.16 Hz, 1 H), 7.51-7.57 (m, 1 H), 7.50 (t, J=72.39 Hz, 1 H), 7.21-7.29 (m, 1 H)

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