I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[CH3:22][Si:23]([C:26]#C)([CH3:25])[CH3:24]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:22][Si:23]([CH3:26])([CH3:25])[C:24]#[C:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:2]=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1
25 g (0.08 mol) Methyl 4-iodo-3-nitrobenzoate (compound IV), 20 ml (0.14 mol) triethylamine and 200 ml tetrahydrofuran were added into a reaction flask, protected by nitrogen gas, and stirred to dissolve, then 2.4 g (0.0034 mol) bis(triphenylphosphine)palladium dichloride, 0.65 g (0.0034 mol) cuprous iodide and 13.7 ml (0.096 mol) trimethylsilylethyne were added, the mixture was reacted at room temperature for 1 hour, concentrated under reduced pressure to evaporated most of the tetrahydrofuran. After extracting with 300 ml ethyl acetate, the organic layer was washed with water for three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness and separated by column chromatography to obtain methyl 4-(2-(trimethylsilyl)ethynyl-3-nitrobenzoate (Compound III), 15.1 g (0.055 mol), yield 66.9%.
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