[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)CC(O)=O>CN(C=O)C.[NH4+].[Cl-].[Cu]I>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:12][CH:11]=1A mixture of 4-methylphenol (30.0 g), 1,4-dibromobenzene (54.5 g), copper(I) iodide (4.40 g), potassium carbonate (5.11 g) and N,N-dimethylglycine (2.86 g) in DMF (300 ml) was stirred at 100° C. under N2 for 18 hr. The mixture was diluted with sat. NH4Cl aq. at 0° C. and extracted with EtOAc. The organic layer was separated, washed with sat. NH4Cl aq., 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with hexane) to give the title compound (39.5 g) as a colorless solid.
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