Triethylamine → 2,2-Difluoroethyl trifluoromethanesulfonate

HRID 19322

Reaction equation

HRID 19322 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(N(CC)CC)C>ClCCl>[F:16][CH:17]([F:20])[CH2:18][O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1361872,2-Difluoroethan-1-ol

Product 1

HCID 27740892,2-Difluoroethyl trifluoromethanesulfonateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

In a flask under argon was placed triflic anhydride (10.22 mL, 61 mmol) and dichloromethane (10 mL) and it was cooled to −70° C. To this cooled mixture was added slowly a solution of 2,2-difluoroethanol (5.00 g, 61 mmol) and triethylamine (8.5 mL, 61 mmol) in dichloromethane (10 mL). After the addition was complete, the mixture was warmed to 25° C. and then concentrated in vacuo. This material was distilled at 60° C. and 50 mm Hg which afforded trifluoro-methanesulfonic acid 2,2-difluoro-ethyl ester (9.74 g, 75%) as a colorless oil.

Workup

  1. customIn a flask under argon was placed
  2. additionAfter the addition
  3. concentrationconcentrated in vacuo
  4. distillationThis material was distilled at 60° C.

Sources & evidence

ORD record
ord-7ce4d0728fee45208e0af46ba190a52b
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Linked notes

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