Reaction #1798

Reaction equation

trifluoromethanesulfonyl chloride

dry ice

2,2,2-Trifluoroethanol

triethylamine

→

2,2,2-trifluoroethyltriflate

Solvents

CH2Cl2

IPA

ether

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGthe mixture was stirred at 0° C. for 30 minutes
3. 3
   FiltrationThe solids were filtered off
4. 4
   Otherthe solvent was removed under reduced pressure with the flask
5. 5
   Temperaturemaintained at 0° C

Procedure

A solution of trifluoromethanesulfonyl chloride (640 μL, 6 mmol) in CH2Cl2 (5 mL) was cooled under argon to -78° C. (IPA:dry ice bath). 2,2,2-Trifluoroethanol was added (365 μL, 5 mmol) and triethylamine (834 μL, 6 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.

Source