[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CC(C)=O.O>[CH2:13]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([F:10])([F:11])[F:12])=[CH:3][C:2]=1[Br:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1A solution of 3-bromo-4-hydroxybenzotrifluoride (6.03 g, 25 mmol) in acetone (1000 ml) was treated with benzyl bromide (4.67 g, 3.25 ml, 27.5 mmol) and potassium carbonate (5.18 g, 37.5 mmol). The mixture was stirred and heated to reflux under nitrogen for 2 h. After cooling, diethyl ether (300 ml) and water (300 ml) were added and the aqueous phase re-extracted with diethyl ether (100 ml). The combined organic layers were washed with water, dried (MgSO4) and the solvent removed in vacuo. The orange oil was flash chromatographed (silica gel, 2-5% dichloromethane-isohexane) to give the title compound as a clear oil (7.0 g, 85%).
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