[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][Si](C)(C)C)=[CH:5][C:4]=1[F:15])[CH3:2].[OH2:16]>O1CCCC1.S(=O)(=O)(O)O.Cl[Hg]Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH3:10])=[CH:5][C:4]=1[F:15])[CH3:2]To a stirred mixture of (4-ethyl-3-fluoro-phenylethynyl)-trimethyl-silane (1.43 g, 6.5 mmol), HgCl2 (250 mg, 0.92 mmol) in aqueous tetrahydrofuran (tetrahydrofuran, 10 mL, H2O, 3 mL), concentrated sulfuric acid (98%, 0.70 mL) was added and the mixture stirred for 6 hours. The mixture was poured into water (50 mL) and extracted with ether (3×20 mL). Removal of solvent gave a solid that was chromatographed (20% thyl acetate/hexanes) to give the desired product. 560 mg, 52%.
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