Ethyl bromoacetate → HCID 57762919, compound

HRID 230599Notes

Reaction equation

HRID 230599 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:16])[CH:5]=[C:6]([F:15])[C:7]=1[C:8]([CH3:14])([CH3:13])[C:9]([F:12])([F:11])[F:10].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][O:16][C:4]1[CH:3]=[C:2]([F:1])[C:7]([C:8]([CH3:13])([CH3:14])[C:9]([F:11])([F:12])[F:10])=[C:6]([F:15])[CH:5]=1)[CH3:23]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 57762931HCID 57762931, compound

Product 1

HCID 57762919HCID 57762919, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetone (5 ml) suspension of 3,5-difluoro-4-(2,2,2-trifluoro-1,1-dimethylethyl)phenol (227 mg, 0.95 mmol), ethyl bromoacetate (174 mg, 1.0 mmol) and potassium carbonate (261 mg, 1.9 mmol) was stirred at reflux for 1 hour. Then, the reaction was quenched with water and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtrated and evaporated to furnish 267 mg (87% yield) of the title compound as colorless oil.

Workup

  1. temperatureat reflux for 1 hour
  2. customThen, the reaction was quenched with water
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltrated
  6. customevaporated

Sources & evidence

ORD record
ord-b7f29996920f4e708e78a5c8e63e80e5
Source dataset
uspto-grants-2009_07
Patent number
US07566739B2

Reaction notes

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