[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-])=O)[CH:3]=1.Cl.[Sn](Cl)[Cl:17]>O>[ClH:17].[NH2:12][C:4]1[CH:3]=[C:2]([Br:1])[C:10]([F:11])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]To a mixture of 4-bromo-5-fluoro-2-nitrobenzoic acid (10 g, 37.9 mmol) and HCl (70 mL, 852 mmol) in water (70 mL) was added tin(II) chloride (21.55 g, 114 mmol) and the mixture was then heated at 90° C. for 3 hours. After cooling to RT, the formed precipitate was filtered, washed with water and collected to give title compound (8.51 g). LCMS (A): m/z [(M−HCl)+H]+ 234/236, C7H5BrFNO2.HCl requires 269/271 (acidic).
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