Acetonitrile → HCID 22467811, compound

Participants

Reaction Conditions

Reaction Steps

Into a 100 mL round bottom flask in a dry box were placed 5.41 g of the 3,5-di(2-bromotetrafluoroethoxy)benzenesulfonyl fluoride, 0.5 g (0.005 mol) of copper(I) chloride and 0.65 g (0.01 mol) of activated zinc powder. Then 15 mL of well-dried acetonitrile was added to the flask. The mixture was stirred at 110° C. under dry nitrogen gas for 2 days, followed by taking a sample for 19F NMR to monitor the progress of the reaction. The spectrum of this sample showed that all of starting material had converted. After being cooled to room temperature, 75 mL of methylene chloride was added to the flask and the organic layer was stirred at room temperature overnight followed by filtration to remove the salt. The combined organic layer was washed with saturated sodium chloride water solution in a 500 mL separatory funnel three times and dried over sodium sulfate overnight. After the removal of the drying agent, the filtrate was refluxed with 5 g of active carbon for 1 day. After being cooled down to room temperature, the mixture was filtered to remove active carbon and the solvents were evaporated off under the reduced pressure. The crude product was purified first by recrystallization and then by column chromatography (silica gel, 70-230 mesh) using 2 parts by volume of petroleum ether to 1 part by volume of chloroform. A total of 2.5 g of 3,5-di(trifluorovinyloxy)benzenesulfonyl fluoride product was obtained as a transparent liquid in about 50% yield.

Provenance & Evidence