Difluoro(fluorosulphonyl)acetyl fluoride → CH2=C(CF2Ocf2CF2SO2F)2

HRID 1178841Notes

Reaction equation

HRID 1178841 reaction equation
[CH2:1]=[C:2]([C:11](OS(F)(=O)=O)([F:13])[F:12])[C:3]([O:6][S:7]([F:10])(=[O:9])=[O:8])([F:5])[F:4].[F:19][S:20]([C:23]([C:26]([O:29][K])([F:28])[F:27])([F:25])[F:24])(=[O:22])=[O:21].[F-:31].[K+].[F:33][S:34]([C:37]([C:40]([F:42])=[O:41])([F:39])[F:38])(=[O:36])=[O:35]>COCCOCCOC.O>[CH2:1]=[C:2]([C:3]([O:6][S:7]([F:10])(=[O:9])=[O:8])([F:5])[F:4])[C:11]([F:13])([F:19])[F:12].[CH2:1]=[C:2]([C:11]([O:41][C:40]([C:37]([S:34]([F:33])(=[O:36])=[O:35])([F:39])[F:38])([F:31])[F:42])([F:13])[F:12])[C:3]([O:29][C:26]([C:23]([S:20]([F:19])(=[O:22])=[O:21])([F:25])[F:24])([F:28])[F:27])([F:5])[F:4]

Participants

8

Reactant 4

HCID 69614Difluoro(fluorosulphonyl)acetyl fluorideHCID 522689Potassium FluorideHCID 10471472CH2=C(CF2Oso2F)2HCID 178527443HCID 178527443, compound

Product 2

HCID 87741755CH2=C(CF3)CF2Oso2FHCID 131726625CH2=C(CF2Ocf2CF2SO2F)2Yield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Conditions

Temperature
20 °C

Procedure

CH2═C(CF2OSO2F)2 is added gradually to FSO2CF2CF2OK, which is prepared from freshly dried KF (3.9 g, 0.067 mole) and FSO2CF2COF (12 g, 0.067 mole) in dry diglyme (30 ml). The resulting mixture is stirred 3 hours at 20° C. The reaction mixture is poured into water. The organic layer is washed with aqueous sodium bicarbonate, then water, and then dried over MgSO4. Distillation gives CH2═C(CF3)CF2OSO2F (0.5 g) and CH2═C(CF2OCF2CF2SO2F)2 (9 g, 58% yield, b.pt. 95–96° C. at 15 mm Hg).

Workup

  1. washThe organic layer is washed with aqueous sodium bicarbonate
  2. dry with materialwater, and then dried over MgSO4
  3. distillationDistillation

Sources & evidence

ORD record
ord-2a360d231027458abc5d04db8e2f8c79
Source dataset
uspto-grants-2007_10
Patent number
US07276624B2

Reaction notes

Loading…