[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1I)([F:4])[F:3].[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C.[Cu](I)I>[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:20]#[C:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([F:4])[F:3]A suspension of PdCl2PPH3 (0.027 g, 0.063 mmol) and copper iodide (0.0035 g, 0.018 mmol) in 3 ml of triethylamine was charged into a 50-ml eggplant flask equipped with a stirrer. To this suspension, a solution of (trifluoromethyl)(2-iodophenyl)sulfide (0.57 g, 1.9 mmol) prepared in Example 1 and phenylacetylene (0.23 g, 2.2 mmol) in 2 ml of triethylamine was added dropwise at room temperature, and the mixture was stirred overnight. After completion of the reaction, a solvent was removed, water was added to the obtained residue, and the mixture was extracted three times with ether. The obtained organic layers was collected and washed with water, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (Benzen/Hexane=20/80) to give target (trifluoromethyl)-(2-(2-phenylethynyl)phenyl)sulfide (0.5 g, 96%).
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