Bromopentafluorobenzene → 3-[(2,3,4,5,6-Pentafluorophenyl)ethynyl]aniline

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A multinecked flash as described in Example 1 was charged with 5.0 g (0.020 mol) of bromopentafluoro-benzene, 2.37 g (0.020 mol) of 3-aminophenylacetylene, 0.096 g (0.137 mmol) of bis(triphenylphosphine) palladium II chloride, 0.148 g (0.564 mmol) of triphenylphosphine, and 0.06 g (0.315 mmol) of cuprous iodide. The reaction mixture was heated at 70° C. for 40 hours after which gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble triethylamine hydrobromide salt by-product followed by concentration of the filtrate gave 5.7 g, (0.02 mol) of crude product as a yellow solid. Short path distillation of the crude under reduced pressure gave 2.84 g (0.010 mol, 50% yield) of the product as a colorless liquid that crystallized on standing.

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