[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].O.F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24]>[Cu]I>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24]A mixture of 2-fluoroaniline (5.0 g), potassium carbonate (2.5 g) and copper(I)iodide (414 mg) in 2-fluoronitrobenzene (16.9 ml) was heated to 180° under nitrogen for 18 h. The cooled mixture was poured into water (300 ml) and extracted with ethyl acetate (2×250 ml) then the combined extracts were washed with saturated brine and evaporated. The residual brown oil was azeotroped with ethanol/water then toluene. The residue was chromatographed with hexane-DE (100:0 to 95:5) to give the title compound (3.25 g) as a bright orange solid, m.p.58°-9°.
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