Nitrogen → Phenylsulfur Pentafluoride

Temperature

-20 °C

A dried 125 mL fluoropolymer (FEP) vessel was flowed with N2 gas and charged with 48.0 g (2.40 mmol) of liquid anhydrous hydrogen fluoride which was cooled at −20° C. The vessel was set with a condenser (made of fluoropolymer) and a thermometer, and cooled in a bath of −20° C. A coolant (−15° C.) was flowed through the condenser. Into the vessel, 8.6 g (0.11 mol) of KF.HF was added. While the mixture was warmed to +15° C., 22.1 g (96.2 mmol) (purity 96 wt % and the other was phenylsulfur trifluoride) of phenylsulfur chlorotetrafluoride was added to the mixture over 1 hour through a syringe. The temperature of the reaction mixture was 3.4° C. and 13.6° C. at the starting point and completing point of the addition, respectively. After the addition, the reaction mixture was stirred at 15° C. for 18 h. After that, the reaction mixture was warmed to 25° C. and hydrogen fluoride was removed under atmospheric pressure. The residue was neutralized with about 15% aqueous KOH and extracted with dichloromethane. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated by distilling the solvent at 70° C. under atmospheric pressure. The resulting residue was distilled under reduced pressure to give 14.4 g (yield 73%) of phenylsulfur pentafluoride (boiling point 57.5° C./35 mmHg). The purity of the product was determined to be 100% by GC analysis. The product was identified by spectral comparison with an authentic reference sample.

1. customThe vessel was set with a condenser
2. customA coolant (−15° C.)
3. additionHF was added
4. temperatureWhile the mixture was warmed to +15° C.
5. additionwas added to the mixture over 1 hour through a syringe
6. customwas 3.4° C. and 13.6° C. at the starting point
7. additionpoint of the addition
8. additionAfter the addition
9. temperatureAfter that, the reaction mixture was warmed to 25° C.
10. customhydrogen fluoride was removed under atmospheric pressure
11. extractionextracted with dichloromethane
12. customThe organic layer was separated
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltered
15. concentrationThe filtrate was concentrated
16. distillationby distilling the solvent at 70° C. under atmospheric pressure
17. distillationThe resulting residue was distilled under reduced pressure

ORD record

ord-edb379cbcab940ca80ee567bef4652a5

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108910B2