N[C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.N(OC(C)(C)C)=O.[ClH:21]>C(#N)C.[Cu](Cl)Cl>[Cl:21][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1(3-Amino-5-(trifluoromethyl)phenyl)methanol (1.0 g, 5.23 mmol) in dry acetonitrile (6 mL) was added dropwise to a solution of copper (II) chloride (0.83 g, 6.2 mmol) and tert-butyl nitrite (0.9 mL, 7.5 mmol) in acetonitrile (6 mL) at 65° C. After 30 min at 65° C., the reaction mixture was cooled to room temperature, poured into a 1 N hydrochloric acid solution, and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) afforded 0.8 g (73%). 1H-NMR (CDCl3, 500 MHz) δ 7.54 (s, 1H), 7.52 (s, 1H), 7.50 (s, 1H), 4.74 (s, 2H).
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