[Br:1]Br.[CH3:3][N:4]([CH3:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.O>[CH3:3][N:4]([CH3:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][C:6]=1[Br:1]Bromine (0.15 ml) was added dropwise to a stirred, cooled (0° C.) mixture of 1-dimethylamino-4-(trifluoromethoxy)benzene (Description 77, 600 mg) and sodium carbonate (620 mg) in chloroform (15 ml). The mixture was stirred for 1 h. and diluted with water. The organic layer was washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with hexane/EtOAc (99:1 increasing to 95:5) to give the title compound as an oil (300 mg). 1H NMR (360 MHz, CDCl3) δ2.79 (6 H, s), 7.06 (1 H, d, J 9 Hz), 7.14 (1 H, dd, J 6, 1.5 Hz), and 7.44 (1 H, d, J 2.0 Hz). m/z (ES+) m/z 270, 272 (M+1).
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