Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15]([OH:19])[CH2:16][C:17]#[CH:18].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>O1CCOCC1.[Cu](I)I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:18]#[C:17][CH2:16][CH2:15][OH:19])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]
4-Bromo-3-(trifluoromethyl)nitrobenzene (500 mg, 1.85 mmol) was dissolved in 1,4-dioxane (10 mL), and but-3-yn-1-ol (389 mg, 5.56 mmol), copper iodide (35 mg, 0.18 mmol), palladium acetate (21 mg, 5 mol %), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl bisphenyl (88 mg, 10 mol %), and cesium carbonate (1207 mg, 3.70 mmol) were added thereto. The resulting mixture was stirred under nitrogen atmosphere at 80° C. for 10 hours, and a saturated ammonium chloride aqueous solution was added thereto to quench the reaction. The reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4-(4-nitro-2-(trifluoromethyl)phenyl)but-3-yn-1-ol (160 mg, 33%) as a brown oil.
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