Triethylamine → 3-[[3-(Trifluoromethyl)phenyl]ethynyl]aniline

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A multinecked round bottom flask fitted with a mechanical stirrer, reflux condenser, and thermometer was flushed and maintained under positive pressure of nitrogen. The flask was charged with 100.0 g (0.44 mol) of 3-bromobenzotrifluoride, 300 ml of dried, degassed triethylamine, 51.5 g (0.44 mol) of 3-aminophenylacetylene, 0.35 g (0.499 mmol) of bis(triphenylphosphine) palladium II chloride, 1.6 g (6.09 mmol) of (triphenylphosphine), and 0.1 g (0.52 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 20 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature followed by the addition of 200 ml of ether. Removal of the triethylamine hydrobromide salt by-product by suction filtration followed by concentration of the filtrate under reduced pressure gave the crude product as a light off-white solid. Short path distillation of the crude product under reduced pressure gave 81.0 g (0.31 mol, 71% yield) of the product as a colorless liquid which crystallized on standing.

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