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

HRID 991438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991438
[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].[I-].[K+]>C1COCC1.O>[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]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 6054722-Bromo-4-fluorophenol

Produkt 1

HCID 22144730Ethyl 2-(2'-bromo-4'-fluorophenoxy)propionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e4f18f327ec0452c9ccf57fab6e76834
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465453B1

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