1-Chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene → 1-Cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene

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To a mixture of 1-chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene (1.5 g, 4.5 mmol) and cyclohexylzinc bromide THF solution (0.5 M, 27 mL) in NMP (30 mL) is added bis(tri-t-butylphosphine)palladium(0) (115 mg, 0.225 mmol). The mixture is purged with N2 for 5 min, followed by heating at 120° C. 12 h under N2. After cooling to room temperature, the reaction is quenched by the addition of H2O (100 mL) and aqueous HCl (1N, 20 mL). The mixture is extracted with EtOAc (3×40 mL). The combined organic phases are washed with saturated aqueous NaHCO3, saturated aqueous NaCl, and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (5% EtOAc in hexanes) to give 1-cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene as a colorless oil.

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