C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1.[OH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=1>C(#N)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:24]=2)=[N:9][CH:10]=1Potassium carbonate (1.4 g) and 2-bromo-5-trifluoromethylpyridine (450 mg) were added to an acetonitrile solution (10 mL) of ethyl 4-hydroxybenzenecarboxylate (221 mg), and heated overnight under reflux. The reaction solution was concentrated under reduced pressure, water was added to the residue and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 4/1) to obtain the entitled compound (330 mg).
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