Trifluoromethanesulfonic anhydride → 2,2-Difluoroethyl trifluoromethanesulfonate
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+]>>[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
4
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 extracted with diethyl ether, dried over MgSO4, and concentrated under reduced pressure to remove the ether. The residue was vaccuum 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
- temperaturecooled with an ice bath
- temperatureThe reaction was cooled in an ice bath
- extractionThe mixture was extracted with diethyl ether
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- customto remove the ether
- distillationdistilled
Sources & evidence
- ORD record
- ord-490846c92a864e36b6c53381b9ed29f3
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293903B2
Reaction notes
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