CC(C)([O-])C.[Na+].F[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[N+:15]([O-:17])=[O:16].[C:18]1([NH2:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>CN(C=O)C>[F:14][C:10]1[C:9]([N+:15]([O-:17])=[O:16])=[C:8]([NH:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][CH:11]=1
Sodium tertbutoxide (1.2 g, 12.58 mmol) was added portionwise to a stirred solution of 1,3-difluoro-2-nitrobenzene (1 g, 6.29 mmol) and phenylamine (1.15 mL, 12.58 mmol) in a hydrous DMF (5 mL) under a nitrogen atmosphere at RT and stirring was continued for 20 h. The mixture was poured into an aqueous solution of NH4Cl and extracted with EtOAc (150 mL). The organic layer was washed with brine, then dried and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-15% EtOAc in cyclohexane) affording (3-Fluoro-2-nitrophenyl)phenylamine as a red solid (1.06 g, 73%). LCMS: RT 3.80 min.
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