P-Xylene → (2,5-Dimethylphenyl)(fluoromethyl)(phenyl)sulfonium tetrafluoroborate

Monofluoromethyl phenyl sulfoxide (1.01 g, 6.38 mmol) of example 2 was dissolved in dry diethyl ether (15 mL) under an argon atmosphere. p-Xylene (0.87 mL, 1.1 eq) was added to the previous solution and then the mixture was cooled to a temperature below −50° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (1.07 mL, 1.0 eq) was added slowly, maintaining the same temperature. The mixture was stirred, at the same temperature, until the reaction was complete. HBF4 in Et2O solution (54%, 1.76 mL, 2 eq) was added and then resulting mixture was stirred for 30 minutes. The solid was isolated by filtration and melt at rt. Saturated solution of NaHCO3 (30 mL) was added to the oily mixture. The resulting mixture was extracted with dichloromethane. The organic phase was dried with magnesium sulfate and concentrated to dryness. 1.486 g of a yellow oily solid was obtained.

1. temperaturethe mixture was cooled to a temperature below −50° C
2. additionwas added slowly
3. temperaturemaintaining the same temperature
4. customresulting mixture
5. stirringwas stirred for 30 minutes
6. customThe solid was isolated by filtration
7. custommelt at rt
8. extractionThe resulting mixture was extracted with dichloromethane
9. dry with materialThe organic phase was dried with magnesium sulfate
10. concentrationconcentrated to dryness

ORD record

ord-13e5813163a347199897a9a0242f5b17

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290446B2