Water → 4-Fluoro-2-nitro-1-phenoxybenzene

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Cs2CO3 (12.1 g, 62.9 mmol) was added to a solution of phenol (5.9 g, 62.9 mmol) in 400 mL of THF under N2. After stirring for 15 min. 2,5-difluoronitrobenzene (6.82 mL, 62.9 mmol) in 50 mL of THF was added. The resulting mixture was heated to 40° C. for 25 h. Reaction was followed by HPLC to detect disappearance of 2,5-difluoronitrobenzene. Water and ethyl acetate were added, followed by extraction with ethyl acetate (2×). The combined organic layers were successively washed with saturated aq. sodium bicarbonate (3×), water and brine, dried (Na2SO4) and evaporated. The crude compound was chromatographed on silica to remove excess of phenol. Elution with toluene/ethyl acetate 95:5 gave the title compound (12.6 g, 86%). Data: (m/z)=234 (M+H)+.

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