Water → Ethyl difluoro(3,4,5-trifluorophenoxy)acetate

HRID 1399417Notes

Reaction equation

HRID 1399417 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:16])[CH:11]=[C:12]([F:15])[C:13]=1[F:14].Br[C:18]([F:25])([F:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].O>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CN(C=O)C>[F:7][C:8]1[CH:9]=[C:10]([CH:11]=[C:12]([F:15])[C:13]=1[F:14])[O:16][C:18]([F:25])([F:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69585Ethyl bromodifluoroacetateHCID 27779433,4,5-Trifluorophenol

Product 1

HCID 21057440Ethyl difluoro(3,4,5-trifluorophenoxy)acetateYield 69.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, 17 g of potassium carbonate and 4.0 g of TBAB were added to 18 g of 3,4,5-trifluorophenol (r-7) dissolved in 200 mL of DMF, 25.0 g of ethyl bromodifluoroacetate dissolved in 50 mL of DMF was added thereto, and the resultant mixture was stirred at 90° C. for 3 hours. A reaction mixture was poured into water, subjected to extraction with diethyl ether, and extracted organic layers were combined and washed with saturated brine, and then dried over anhydrous magnesium sulfate. A solvent was evaporated under reduced pressure, and thus 22.8 g of ethyl 2-(3,4,5-trifluorophenoxy)-2,2-difluoroacetate (compound (r-8)) was obtained.

Workup

  1. additionwas added
  2. extractionsubjected to extraction with diethyl ether
  3. extractionextracted organic layers
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customA solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5dd0b2eeefca409d8c1d31b7a20ad022
Source dataset
uspto-grants-2014_12
Patent number
US08906260B2

Reaction notes

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