Br[C:2]1[CH:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].C(N(CC)CC)C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(#N)C>[CH3:8][Si:9]([CH3:11])([CH3:10])[C:12]#[C:13][C:2]1[CH:3]=[C:4]([CH3:7])[S:5][CH:6]=1A mixture of 4-bromo-2-methylthiophene (1.00 g), trimethylsilyl acetylene (1.17 mL), bis(triphenylphosphine) palladium(II) dichloride (119 mg), copper(I) iodide (65 mg), triethylamine (1.57 mL), and acetonitrile (15 mL) was stirred at 80° C. for 4 hours under an argon atmosphere. The reaction mixture was left to be cooled and filtrated through a Celite (registered trademark) pad. To the filtrate was added saturated brine, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (605 mg). 1H-NMR (CDCl3) δ ppm: 0.23 (9H, s), 2.44 (3H, d, J=1.0 Hz), 6.75-6.80 (1H, m), 7.21-7.25 (1H, m).
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