Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:10]=[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=12-Bromo-4-trifluoromethyl-benzoic acid (100 mg, 0.372 mmol) and phenylboronic acid (70 mg, 0.574 mmol) were dissolved in 6 mL dioxane and 3 mL 1N sodium carbonate solution. The mixture was evacuated and back-filled with argon several times to remove oxygen. 2-Dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (S-Phos, 31 mg, 0.075 mmol) and palladium acetate (8 mg, 0.036 mmol) were added and the reaction mixture was refluxed overnight. The mixture was diluted with ethyl acetate, water and 2N sodium carbonate solution. The mixture was extracted three times with 2N sodium carbonate solution and the aqueous layers washed with ethyl acetate. The combined organic layers were discarded. The combined aqueous layers were acidified with 2N HCl and extracted twice with dichloromethane. The organic layers were washed with brine, combined, dried over sodium sulfate, filtered and concentrated down. Purification of the residue by flash chromatography on gel with dichloromethane/methanol/acetic acid (100:0:0→90:10:0.5) yielded the title compound as a white solid (63 mg, 64%).
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