Acetonitrile → HCID 22467811, compound

Temperature

110 °C

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.

1. customInto a 100 mL round bottom flask in a dry box were placed
2. customthe progress of the reaction
3. temperatureAfter being cooled to room temperature
4. stirringthe organic layer was stirred at room temperature overnight
5. filtrationfollowed by filtration
6. customto remove the salt
7. washThe combined organic layer was washed with saturated sodium chloride water solution in a 500 mL separatory funnel three times
8. dry with materialdried over sodium sulfate overnight
9. customAfter the removal of the drying agent
10. temperaturethe filtrate was refluxed with 5 g of active carbon for 1 day
11. temperatureAfter being cooled down to room temperature
12. filtrationthe mixture was filtered
13. customto remove active carbon
14. customthe solvents were evaporated off under the reduced pressure
15. customThe crude product was purified first by recrystallization

ORD record

ord-9bdb84563ed0419993062322233305ee

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268532B1