FC(F)(F)c1cccc(Br)c1.OC1CCNCC1>C1COCCO1.CC(=O)O.CC(=O)O.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>OC1CCN(c2cccc(C(F)(F)F)c2)CC1A mixture of 1-bromo-3-(trifluoromethyl)benzene (6.13 mL, 44.44 mmol), piperidin-4-ol (5.608 g, 55.44 mmol), diacetoxypalladium (0.200 g, 0.89 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.553 g, 0.89 mmol) and cesium carbonate (18.10 g, 55.55 mmol) in dioxane (100 mL) was evacuated and backfilled with N2 three times and then it was heated at 100 °C for 6h. The mixture was filtered through filter agent(supercell), washed with EtOAc. The combined filtrate was concentrated. The residue was purified by silica gel column(0-35% EtOAc/hexane) to give 1-(3-(trifluoromethyl)phenyl)piperidin-4-ol (4.70 g, 43.1 %) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) d 7.38 (t, _J_ = 8.03 Hz, 1H), 7.20 (dd, _J_ = 2.38, 8.41 Hz, 1H), 7.13 (s, 1H), 7.00 (d, _J_ = 7.78 Hz, 1H), 4.64 - 4.72 (m, 1H), 3.53 - 3.72 (m, 3H), 2.93 (ddd, _J_ = 3.01, 9.98, 12.86 Hz, 2H), 1.71 - 1.88 (m, 2H), 1.45 (dtd, _J_ = 3.89, 9.44, 12.86 Hz, 2H). LCMS 246.
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