4-Bromobiphenyl → 5-(1,1'-Biphenyl-4-yl)-4-pentyn-1-ol

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4-Bromobiphenyl (10.28 g, 44.10 mmol), 4-pentyn-1-ol (4.45 g, 52.92 mmol), and bis(triphenylphosphine)palladium(II) dichloride (310 mg, 0.44 mmol) were stirred in triethylamine (100 mL) under nitrogen for 5 min. Copper(I) iodide (42 mg, 0.22 mmol) was added, and the mixture was stirred for 4 hrs at 65° C. The mixture was cooled to room temperature and filtered through a celite pad, rinsed with ethylacetate. The combined filtrate was evaporated to dryness under reduced pressure. The resulting residue was purified by column chromatography (hexanes:ethylacetate 3:2) to afford 7.78 g of the title compound. Yield: 75%. 1H NMR (300 MHz, CDCl3) δ 1.88 (m, 2H), 2.57 (t, J=6.9 Hz, 2H), 3.84 (t, J=6.0 Hz, 2H), 7.32-7.60 (m, 9H) ppm; 13C NMR (75 MHz, CDCl3) δ 16.4, 31.7, 62.1, 81.2, 90.2, 122.8, 127.0, 127.1, 127.6, 128.9, 132.0, 140.1 ppm.

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