Ethyl bromoacetate → Ethyl 4-(2-chloro-4-trifluoromethylphenoxy)phenoxyacetate

HRID 844918Notes

Reaction equation

HRID 844918 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 129406134-[2-Chloro-4-(trifluoromethyl)phenoxy]phenol

Product 1

HCID 14030465Ethyl 4-(2-chloro-4-trifluoromethylphenoxy)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1.44 parts of 4-(2-chloro-4-trifluoromethylphenoxy)phenol, 0.84 part of ethyl bromoacetate, and 1.38 parts of anhydrous potassium carbonate were refluxed for 3 hours in 20 parts by volume of methyl ethyl ketone in an atmosphere of nitrogen. After the reaction, the reaction mixture was filtered. The filtrate was concentrated, and water was added. The mixture was then extracted with ethyl acetate. The extract was washed with a 1N aqueous solution of sodium hydroxide and then with water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 1.5 parts of ethyl 4-(2-chloro-4-trifluoromethylphenoxy)phenoxyacetate.

Workup

  1. customAfter the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. additionwater was added
  5. extractionThe mixture was then extracted with ethyl acetate
  6. washThe extract was washed with a 1N aqueous solution of sodium hydroxide
  7. dry with materialwith water, and dried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e3007bbb3cd54100847a3d72bab26558
Source dataset
uspto-grants-1988_07
Patent number
US04755209

Reaction notes

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