[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[C:3]=1[F:11].B1([O-])OO1.[OH2:16].[OH2:17].O.O.[Na+].O>C(O)(C(F)(F)F)=O.C(O)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N+:6]([O-:17])=[O:16])=[C:4]([O:9][CH3:10])[C:3]=1[F:11]To 4-bromo-3-fluoro-2-methoxyaniline (1 g, 4.5 mmol) in a mixture of TFA and acetic acid (10 mL/10 mL) was added sodium perborate tetrahydrate (3.2 g, 21 mmol). The reaction mixture was warmed up to 60° C. and heated for 24 h. It was then diluted to water, extracted with ethyl acetate. The product was obtained by flash column as a yellow solid (450 mg, 40%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.11 (s, 3H) 7.40 (dd, J=9.0, 6.2 Hz, 1H) 7.54 (dd, J=9.0, 1.9 Hz, 1H).
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