[F:1][C:2]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].CC([O-])=O.[K+].[Br:18]Br>CC(O)=O>[Br:18][C:5]1[CH:6]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:8]=[C:2]([F:1])[C:3]=1[NH2:4]A mixture of 2-fluoro-4-methylsulfonyl-aniline (22.76 mmol) and KOAc (22.7 mmol) in AcOH was stirred at room temperature. The mixture was cooled to 0° C. and Br2 (22.7 mmol) was added dropwise. The mixture was stirred for 30 min at 0° C. The mixture was concentrated and the residue was taken up in EtOAc. The organic mixture was washed (sat. NaHCO3, sat. Na2S2O3), dried (Na2SO4) and concentrated to yield the desired product.
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