[F:1][C:2]1[C:8](F)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[C:8]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4]To a solution of 2,3-difluoro-6-nitroaniline (200 mg, 1.15 mmol) in DMF (10 ml) was added phenol (108 mg, 1.15 mmol) and potassium carbonate (317 mg, 2.30 mmol). The reaction was heated (120° C.) overnight and then cooled to rt. The reaction was diluted with ethyl acetate (200 mL) and then washed with water (2×100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using 0-50% ethylacetate/hexane to afford the desired product (267 mg, 94%) 1H NMR (300 MHz, DMSO-d6) 7.85 (dd, J=9.8, 2.2 Hz, 1H), 7.34-7.49 (m, 4H), 7.19-7.27 (m, 1H), 7.08-7.16 (m, 2H), 6.21 (dd, J=9.7, 7.8 Hz, 1H); HPLC RT (Method A) 3.48 min.
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