Toluene → 2'-Benzyloxy-2-bromobiphenyl

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A solution of 2-benzyloxyphenylboronic acid (4.3 g. 19.3 mmol) and 1,2-dibromobenzene (9.11 g, 4.66 ml, 38.6 mmol) in 1:1 toluene:ethanol (150 ml) was stirred under nitrogen and tetrakis(triphenylphosphine)palladium(0) (1.12 g, 0.95 mmol) and potassium carbonate (21.3 g, 154 mmol) added. The reaction was stirred at 90° C. under nitrogen for 2 hours. After cooling, diethyl ether (100 ml) and water (100 ml) were added and the organic phase separated. The aqueous phase was extracted with diethyl ether (50 ml) and the combined organic layers washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was flash chromatographed (silica gel, 5-15% CH2Cl2-isohexane) to give the title compound as a clear oil (4.53 g, 69%).

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