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

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.

1. washwashed with water (10 mL)
2. washwashed with brine (10 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationConcentration
5. customfollowed by purification by silica gel chromatography with hexanes

ORD record

ord-78e2550ee3524a9abd90eac3bf4544da

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354398B2