Trifluoromethanesulfonic anhydride → 4,4,5,5,5-Pentafluoropentyl trifluoromethanesulfonate

HRID 1443583Notes

Reaction equation

HRID 1443583 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[CH2:18][CH2:19][CH2:20]O>>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][CH2:20][CH2:19][CH2:18][C:17]([F:26])([F:16])[C:22]([F:25])([F:24])[F:23])(=[O:8])=[O:9]

Participants

3

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

Product 1

HCID 866125674,4,5,5,5-Pentafluoropentyl trifluoromethanesulfonateYield 33.3%

Procedure

At 0° C., 18.6 g of trifluoromethanesulfonic anhydride was added dropwise to 10.7 g of 4,4,5,5,5-pentafluoropentanol. The mixture was stirred at room temperature for an hour and then at 80° C. for 2 hours. Thereafter, the reaction mixture was poured into ice water and then extracted with t-butyl methyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 6.2 g of 4,4,5,5,5-pentafluoropentyl trifluoromethanesulfonate.

Workup

  1. extractionextracted with t-butyl methyl ether
  2. washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abee8bf7fbd8468b836350a1410f9393
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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