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

HRID 18818Notes

Reaction equation

HRID 18818 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-99356e1627bb4107842395945d2688b4
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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