[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>C(#N)C.[Cu](I)I.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.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:4][CH:3]=1
To a solution of 4-chloroiodobenzene (4.77 g:0.02 mole) in dry acetonitrile (30 ml) and triethylamine (2.02 g:0.02 mole) under nitrogen, was added copper iodide (0.2 g:1.05 mole), bis (triphenylphosphine)palladium dichloride (0.2 g=0.285 mmole) and trimethylsilylethyne (2.156 g:0.022 mole). The mixture was stirred for three hours during which time there was an exotherm at 20° C. and a darkening of the reacton mixture. The mixture was poured into saturated ammonium chloride solution (100 ml) and was extracted with ether (×3). The extracts were combined, washed with dilute hydrochloric acid and dried over magnesium sulfate and then filtered through charcoal. Removal of solvent in vacuo gave a brown oil which was titurated with hexane and filtered to remove by-products. The filtrate was evaporated to give yellow crystals (3.90 g).
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