Example 2
Overall Experimental
Bromoethane, copper(I) oxide, bromine, anhydrous N,N-dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), charcoal, and 1,4-dioxane were purchased from Sigma Aldrich. Phenothiazine and copper iodide were obtained from Acros Organics. Sodium hydride, sodium acetate, and acetic acid were purchased from Alfa Aesar. Pentafluorothiophenol and sodium pentafluoropropionate were purchased from Oakwood Chemical, iron powder from Mallinckrodt Pharmaceuticals, 2,3,4,5-tetrafluoroaniline from AK Scientific, potassium hydroxide and celite from Fisher Scientific, and ethanol from Decon Labs. All reagents were used without further purification.
Silica gel (65×250 mesh) was purchased from Sorbent Technologies, and solvents for purification were purchased from VWR International. 1H, 19F and 13C NMR spectra were obtained on 400 MHz Varian NMR spectrometers in DMSO-d6, acetone-d6 or CDCl3 purchased from Cambridge Isotope Laboratories. 19F NMR spectra were recorded in CDCl3 using hexafluorobenzene (Alfa Aesar) as an internal standard, and the chemical shifts are reported vs. CFCl3 at 0 ppm by adjusting the shift of hexafluorobenzene to −164.9 ppm. Mass spectra were obtained on an Agilent 5973 Network mass-selective detector attached to Agilent 6890N Network GC system. Elemental analyses were performed by Atlantic Microlab, Inc.
