Potassium Carbonate → Ethyl 2-(2'-bromo-4'-fluorophenoxy)propionate

HRID 1815798Notes

Reaction equation

HRID 1815798 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].Br[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+]>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 22144730Ethyl 2-(2'-bromo-4'-fluorophenoxy)propionateYield 87%

Reagents, catalysts & solvents 1

HCID 4875Potassium IodideCatalyst

Procedure

A mixture of 15 gm (78.5 mMol) 2-bromo-4-fluorophenol, 11.2 mL (86.4 mMol) ethyl 2-bromopropionate, and 13 gm (94.2 mMol) potassium carbonate was heated at reflux for 3 hours. At this point 0.1 gm potassium iodide were added and reflux continued for another 2 hours. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the aqueous phase was extracted well with ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with hexane containing 5% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 19.8 gm (87%) of the desired compound as a clear oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperaturereflux
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted well with ethyl acetate
  7. washwashed with saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washeluting with hexane containing 5% ethyl acetate
  11. additionFractions containing product
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80f11f98d13d426ea1ca5be4f2b34d17
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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