Ethyl chloroacetate → Ethyl 2-(3-fluorophenoxy)acetate

HRID 1929092Notes

Reaction equation

HRID 1929092 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([O:11][C:12](=[O:15])[CH2:13]Cl)[CH3:10].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:9]([O:11][C:12](=[O:15])[CH2:13][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH3:10]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 97433-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 15078057Ethyl 2-(3-fluorophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

3-Fluoro-phenol (100 g, 892 mmol) is dissolved in acetone (250 ml) and after addition of chloro-acetic acid ethyl ester (114 ml, 1.07 mol) and K2CO3 (249 g, 1.78 mol) the mixture is refluxed for 24 h. After cooling down to 0° C., the mixture is filtrated and the filtrate is evaporated under reduced pressure. Yield: 198 g (100%) of a red oil.

Workup

  1. temperatureis refluxed for 24 h
  2. filtrationthe mixture is filtrated
  3. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3917699bc0c479f86a0dff5bf8afec0
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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