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

HRID 2304619Notes

Reaction equation

HRID 2304619 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1.O.[I-].[K+]>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

7

Reactant 3

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

Product 1

HCID 22144730Ethyl 2-(2'-bromo-4'-fluorophenoxy)propionateYield 86.6%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Scheme IA, step A: 2-bromo-4-fluorophenol (15.0 g, 78.5 mmol) was dissolved in THF (200 mL) and treated with potassium carbonate (13.0 g, 94.2 mmol) and ethyl 2-bromopropionate (11.2 mL, 86.4 mmol). The reaction mixture was heated at reflux for 3 hours. Potassium iodide (0.1 g) was added and the reaction mixture was stirred for an additional 2 hours at reflux. The reaction was then cooled, diluted with water and extracted with ethyl acetate. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography to provide ethyl 2-(2′-bromo-4′-fluorophenoxy)propionate (19.8 g) as a clear oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureat reflux
  4. temperatureThe reaction was then cooled
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2c2224f7bdad4219b5de4323b911963c
Source dataset
uspto-grants-2002_08
Patent number
US06436964B1

Reaction notes

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