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Ethyl bromoacetate → Ethyl 2-(2,2,2-trifluoroethoxy)phenoxyacetate

HRID 273850
Notes
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Reaction equation

HRID 273850 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]([F:12])([F:13])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl Acetate2×HCID 11430Potassium CarbonateHCID 130853472-(2,2,2-Trifluoroethoxy)phenol

Product 1

HCID 20094388Ethyl 2-(2,2,2-trifluoroethoxy)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 2-(2,2,2-trifluoroethoxy)phenol (200 mg) in dry N,N-dimethylformamide (2 ml) were added ethyl bromoacetate (138 μl) and potassium carbonate (216 mg), and the mixture was reacted with stirring at room temperature for 1 hour, and then for 1 hour at 60° C. To the reaction mixture was added ethyl acetate, and ethyl acetate solution was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 270 mg of ethyl 2-(2,2,2-trifluoroethoxy)phenoxyacetate as an oil.

Workup

  1. customthe mixture was reacted
  2. waitfor 1 hour at 60° C
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8869df0e4dd243f28484cedfe31b98a8
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05387603

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes