N,N,N',N'-Tetramethylethylenediamine → Diethyl 2,2-difluoropentanedioate

HRID 1260400Notes

Reaction equation

HRID 1260400 reaction equation
Br[C:2]([F:9])([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].CN(CCN(C)C)C>O1CCCC1.[Cu]>[CH2:6]([O:5][C:3](=[O:4])[C:2]([F:9])([F:8])[CH2:12][CH2:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])[CH3:7]

Participants

6

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8821Ethyl AcrylateHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 20455495Diethyl 2,2-difluoropentanedioate

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Commercially available ethyl bromodifluoroacetate (16 mL, 120 mmol) and ethyl acrylate (11 mL, 100 mmol) were dissolved in tetrahydrofuran (100 mL), and copper powder (15.2 g, 240 mmol) and TMEDA (16.7 mL, 110 mmol) were sequentially added thereto at room temperature. After stirring for about 8 hours, the reaction was terminated by the addition of a saturated aqueous solution of 1.0 N hydrochloric acid and was extracted two times with toluene. The reaction solution was distilled under reduced pressure and the concentrated title compound was directly used in the subsequent step without further purification.

Workup

  1. customat room temperature
  2. customthe reaction was terminated by the addition of a saturated aqueous solution of 1.0 N hydrochloric acid
  3. extractionwas extracted two times with toluene
  4. distillationThe reaction solution was distilled under reduced pressure
  5. concentrationthe concentrated title compound
  6. customwas directly used in the subsequent step without further purification

Sources & evidence

ORD record
ord-32646289684749748d218a4939a65328
Source dataset
uspto-grants-2013_06
Patent number
US08470836B2

Reaction notes

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