Trimethylsilylacetylene → 3-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

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A mixture of 3-bromo-2-iodo-5-(trifluoromethyl)aniline (5.21 g), ethynyl(trimethyl)silane (2.21 mL), triethylamine (100 mL), dichlorobis(triphenylphosphine)palladium(II) (1.00 g) and copper(I) iodide (0.271 g) was stirred overnight at 80° C. under nitrogen atmosphere. The solvent was evaporated under reduced pressure, to the residue was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.70 g).

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