[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:14][O:15][C:16](=[O:28])[C:17]1[C:22]([F:23])=[C:21]([F:24])[C:20](Br)=[C:19]([F:26])[C:18]=1[F:27].C1(B(O)O)C=CC=CC=1>O>[CH3:14][O:15][C:16]([C:17]1[C:22]([F:23])=[C:21]([F:24])[C:20]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:19]([F:26])[C:18]=1[F:27])=[O:28]A mixture of toluene (370 mL) and water (70 mL) was degassed with nitrogen for 30 minutes. A mixture of cesium carbonate (102.6 g, 315 mmol), 4-bromo-2,3,5,6-tetrafluoro-benzoic acid methyl ester (30.0 g, 105 mmol), phenyl boronic acid (19.26 g, 157 mmol) and tetrakis triphenyl phosphene palladium(0) (11.5 g, 9.9 mmol) were added to the above degassed water/toluene mixture. The reaction mixture was refluxed overnight. After the reaction is completed, it was cooled to room temperature and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated. The resulting residue was purified by column chromatography using 5% ethyl acetate in hexane to obtain the title compound (26.5 g, 88.6%).
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