Triethylamine → 4-[(3-Aminophenyl)ethynyl]-phenyl Trifluoromethyl Sulfide

Participants

Reaction Conditions

Reaction Steps

A multinecked flask as described in Example 1 was charged with 5.4 g (0.021 mol) of p-bromophenyl trifluoromethyl sulfide, 75 ml of dried, degassed triethylamine, 2.46 g (0.021 mol) of 3-aminophenylacetylene, 0.048 g (0.068 mmol) of bis(triphenylphosphine) palladium II chloride, 0.0148 g (0.564 mmol) of triphenylphosphine, and 0.03 g (0.157 mmol) of cuprous iodide. The reaction mixture was heated at 75° C. for 20 hours after which gas chromatography showed the reaction to be complete. The 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 the crude product in near quantitative yield as an off-white solid. Short path distillation of the crude product under reduced pressure gave 3.9 g (0.013 mol, 62% yield) of the purified product as a white solid.

Provenance & Evidence