[Br:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:17]([CH3:19])[CH3:18]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:17]([CH3:19])[CH3:18])[C:3]=1[F:9]To a mixture of 3-bromo-2-fluoro-phenol (2 g, 10 mmol) and cesium carbonate (10 g, 40 mmol) in acetonitrile (20 mL) was added 2-bromopropane (4 mL, 50 mmol). The reaction mixture was stirred at 80° C. for 4 h. The mixture was filtered through a plug of Celite and eluted with ethyl acetate. The resulting solution was evaporated. The residue was purified by flash chromatography on silica gel and eluting with hexanes:EtOAc (1:1) to afford the title product (1.7 g).
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