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Carbon Dioxide → 2,2,2-Trifluoroethyl trifluoromethanesulfonate

HRID 1703
Notes
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Reaction equation

HRID 1703 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3](Cl)(=[O:5])=[O:4].C(=O)=O.[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15].C(N(CC)CC)C>C(Cl)Cl.CCOCC.CC(O)C>[F:12][C:13]([F:17])([F:16])[CH2:14][O:15][S:3]([C:2]([F:8])([F:7])[F:1])(=[O:5])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 64092,2,2-TrifluoroethanolHCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Reagents, catalysts & solvents 3

HCID 3283Diethyl Ether
Solvent
HCID 3776IsopropanolSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of trifluoromethanesulfonyl chloride (800 uL, 7.5 mmole) in CH2Cl2 (6 mL) was cooled under argon to -60° C. (IPA:dry ice bath). 2,2,2-Trifluoroethanol was added (456 uL, 6 mmol) and triethylamine (1.04 uL, 7.5 mmol) was added dropwise. The reaction was stirred for 1.5 hours then warmed to 0° C. for 1 hour. Anhydrous ether (20 mL) was added and the mixture was stirred at 0° C. for 30 minutes. The solids were filtered off and the solvent was removed under reduced pressure with the flask maintained at 0° C. This afforded the 2,2,2-trifluoroethyltriflate as a yellow oil which was used immediately.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at 0° C. for 30 minutes
  3. filtrationThe solids were filtered off
  4. customthe solvent was removed under reduced pressure with the flask
  5. temperaturemaintained at 0° C

Sources & evidence

ORD record
ord-c1eb50330c204669ac80b93517bb8dec
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726172

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes