2,2,2-Trifluoroethanol → 2,2,2-Trifluoroethyl Methanesulfonate

HRID 1293134Notes

Reaction equation

HRID 1293134 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(OCC)(=O)C>[CH3:14][S:15]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 5565652,2,2-Trifluoroethyl Methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,2,2-trifluoroethanol (5 g), triethylamine (14 ml) and ethyl acetate (120 ml) was added dropwise methanesulfonyl chloride (5.8 ml) with cooling it on ice, and stirred at this temperature for 1 hour. The reaction solution was filtered through a small amount of silica gel, followed by NH silica gel, which in turn was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to yield the title compound (9.5 g).

Workup

  1. temperaturewith cooling it on ice
  2. filtrationThe reaction solution was filtered through a small amount of silica gel
  3. washwas washed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a88b9f9f54eb4c4da93ab47877dba86f
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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