Ethyl bromoacetate → Ethyl 2-(4-fluorophenoxy)acetate

HRID 1633203Notes

Reaction equation

HRID 1633203 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(C(C)=O)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 4476170Ethyl 2-(4-fluorophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 13.8 g (0.1 mole) potassium carbonate, 11.3 g (0.01 mole) 4-fluorophenol and 13.0 ml (19.6 g [0.22 mole]) ethyl bromoacetate in 100 ml methyl ethyl ketone were stirred overnight at room temperature and then heated at reflux for 5 hours. After the reaction mixture cooled to room temperature, it was filtered. The filtrate was concentrated to remove solvent. The concnetrate was used as a whole without further isolation in Example 2.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter the reaction mixture cooled to room temperature
  4. filtrationit was filtered
  5. concentrationThe filtrate was concentrated
  6. customto remove solvent

Sources & evidence

ORD record
ord-20582e093e164f9e8bd19dc4ab7bb4f8
Source dataset
uspto-grants-1984_10
Patent number
US04479900

Reaction notes

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