Triethylamine → 2-Bromo-2,2-difluoroethyl pivalate

HRID 558044Notes

Reaction equation

HRID 558044 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:8][C:9]([F:13])([F:12])[CH2:10][OH:11].C(N(CC)CC)C>O1CCCC1>[C:1]([O:11][CH2:10][C:9]([Br:8])([F:13])[F:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 183684762-Bromo-2,2-difluoroethan-1-ol

Product 1

HCID 578173452-Bromo-2,2-difluoroethyl pivalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pivalic chloride and 2-bromo-2,2-difluoroethanol were mixed in tetrahydrofuran and ice cooled. Triethylamine was added to the mixture. Subsequent standard separatory operation and solvent distillation gave 2-bromo-2,2-difluoroethyl pivalate. This compound was converted into a sodium sulfinate using sodium dithionite and then oxidized with hydrogen peroxide, yielding the target compound, sodium 2-(pivaloyloxy)-1,1-difluoroethanesulfonate.

Workup

  1. temperatureice cooled
  2. distillationSubsequent standard separatory operation and solvent distillation

Sources & evidence

ORD record
ord-9c40d4df90064dec910bb32118f834a3
Source dataset
uspto-grants-2011_11
Patent number
US08062828B2

Reaction notes

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