Water → 2-Fluoroethyl trifluoromethanesulfonate

HRID 1046258Notes

Reaction equation

HRID 1046258 reaction equation
[F:1][CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[O:12](S(C(F)(F)F)(=O)=O)[S:13]([C:16]([F:19])([F:18])[F:17])(=O)=[O:14].O>ClCCl>[F:17][C:16]([F:19])([F:18])[S:13]([O:4][CH2:3][CH2:2][F:1])(=[O:14])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 97372-FluoroethanolHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 136389352-Fluoroethyl trifluoromethanesulfonateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 2-fluoroethanol (3.2 g, 50 mmol) and triethylamine (5.5 g, 55 mmol) in dichloromethane (60 mL) was added dropwise (CF3SO2)2O (15.5 g, 55 mmol) at −78° C. under N2. The mixture was stirred at 10-20° C. for 1 h, and treated with water (100 mL). The organic layer was washed with satd aq NaHCO3 (100 mL) and brine (100 mL), dried, and concentrated to give 2-fluoroethyl trifluoromethanesulfonate (8 g, yield 82%).

Workup

  1. washThe organic layer was washed with satd aq NaHCO3 (100 mL) and brine (100 mL)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6220bf4ccbca4e209236260e6a99f3e0
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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