Potassium Carbonate → (4'-Fluorobiphenyl-4-yl)(phenyl)methanol

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To a solution of 11 (1 g, 3.80 mmol) and 4-fluorophenyl boronic acid (585 mg, 4.18 mmol) in a 2:1 mixture of DME:water (30 mL), was added Pd(PPh3)4 (307 mg, 0.27 mmol), tri-o-toly phosphine (81 mg, 0.27 mmol) and potassium carbonate (2.63 g, 19.0 mmol). The solution was heated to 80° C. and stirred for 16 hours. Then water (50 mL) was added and the organic residue was extracted with ethyl acetate (2×40 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (2-50%) in hexane to afford compound 12 as a white solid (600 mg, 57%). 1H NMR (DMSO-d6) δ (ppm): 7.67-7.63 (m, 2H), 7.56 (d, J=8.4 Hz, 2H), 7.45-7.38 (m, 4H), 7.32-7.17 (m, 5H), 5.93 (d, J=3.9 Hz, 1H), 5.73 (d, J=3.8 Hz, 1H).

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