1,1,1-Trifluoro-3-iodopropane → Benzene, (5,5,5-trifluoro-1-pentyn-1-yl)-

Participants

Reaction Steps

To a solution of 1,1,1-trifluoro-3-iodopropane (0.052 mL, 0.438 mmol), Pd2(dba)3 (24.0 mg, 0.026 mmol), Tri-2-furylphosphine (10.2 mg, 0.044 mmol) and copper(I) iodide (8.33 mg, 0.044 mmol) in N,N-dimethylformamide (2.5 mL) was added tributyl(phenylethynyl)stannane (0.178 mL, 0.481 mmol) under nitrogen. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (10 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification by silica gel chromatography with hexanes yielded (5,5,5-trifluoropent-1-ynyl)benzene (50 mg). The compound had an HPLC ret. time=4.08 min.−Column: YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100.

Provenance & Evidence