Trifluoromethanesulfonic anhydride → 2,2-Difluoroethyl trifluoromethanesulfonate

HRID 1844308Notes

Reaction equation

HRID 1844308 reaction equation
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[F:16][CH:17]([F:20])[CH2:18]O.C([O-])(O)=O.[Na+]>C(OCC)C>[F:15][C:12]([F:13])([F:14])[S:9]([O:8][CH2:18][CH:17]([F:20])[F:16])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 1361872,2-Difluoroethan-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 27740892,2-Difluoroethyl trifluoromethanesulfonateYield 64.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
84 °C

Procedure

Triflic anhydride (27.9 g, 99.1 mmol) was placed in a flask and cooled with an ice bath. 2,2-Difluoroethanol (8.1 g, 99.1 mmol) was added and the reaction was heated to 84° C. for 1 hour. The reaction, was cooled in an ice bath and poured into 100 ml cold 5% NaHCO3 solution. The mixture was attracted with diethyl ether, dried over MgSO4, and concentrated under reduced pressure to remove the ether. The residue was vacuum distilled to give 2,2-difluoroethyl trifluoromethanesulfonate as a clear liquid (13.6 g, 64%, bp −55° C.). 1H NMR (400 MHz, CDCl3) δ ppm 6.17-5.88 (1H), 4.61-4.13 (2H)

Workup

  1. temperaturecooled with an ice bath
  2. customThe reaction
  3. temperaturewas cooled in an ice bath
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto remove the ether
  7. distillationdistilled

Sources & evidence

ORD record
ord-1b106d1b53ef4ab082cb38b7c0cce862
Source dataset
uspto-grants-2015_02
Patent number
US08946413B2

Reaction notes

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