[CH2:1]([C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[CH:7][C:8]=1[Cl:9])[CH3:2].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)Cl>>[Cl:9][C:8]1[CH:7]=[CH:6][C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[CH2:1][CH3:2]3-ethyl-4-chlorophenol (2.0 g, 0.013 mol), phenylboronic acid (4.7 g, 0.038 mol), TEA (11 mL, 0.077 mol), cupric acetate (4.2 g, 0.023 mol) and DCM (60 mL, 0.9 mol) were added to a 100 mL oven dried flask and the reaction was stirred at rt for 24 h. The solvent was then removed under reduced pressure and the resulting residue was purified by flash chromatography (5% EtOAc in Hexane).
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