Diethyl Ether → Ethyl 2-(3-fluorophenoxy)acetate

HRID 2053609Notes

Reaction equation

HRID 2053609 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CCOCC>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 97433-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 15078057Ethyl 2-(3-fluorophenoxy)acetateYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-fluorophenol (2.24 g, 20.0 mmol) in DMF (40 mL) is added potassium carbonate (3.03 g, 22.0 mmol) and ethyl bromoacetate (2.34 mL, 21.0 mmol), and the mixture is stirred at 70° C. for 18 h. The mixture is cooled to RT, Et2O is added, and the mixture is washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is vacuum distilled to give 3.2 g of the product 432.

Workup

  1. temperatureThe mixture is cooled to RT
  2. washthe mixture is washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. distillationdistilled

Sources & evidence

ORD record
ord-5f63cf26b0bb497c8ae2a318b7dbd2ec
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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