Potassium Carbonate → HCID 68431677, Verbindung

HRID 889242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889242
[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([F:17])[C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27]>CN(C=O)C>[CH3:29][O:28][C:26](=[O:27])[CH2:25][NH:11][C:10]1[C:12]([F:17])=[CH:13][C:14]([Br:16])=[CH:15][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate2×HCID 684315652-(Benzyloxy)-4-bromo-6-fluoroaniline

Produkt 1

HCID 68431677HCID 68431677, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 2.6 g (8.78 mmol) of 2-benzyloxy-4-bromo-6-fluoroaniline and 3.03 g (21.96 mmol) of potassium carbonate in 20 mL DMF in an oil bath at 60° C. is added 1.48 g (9.67 mmole) of methyl bromoacetate. The mixture is stirred at 60° C. for 2 h. HPLC analysis indicated that the reaction is 38% complete. Additional methyl bromoacetate equal to the molar amount of unreacted starting material is added and the mixture is stirred at 60° C. for 2 h. This process is repeated until the starting material is nearly consumed. The mixture is allowed to cool then is poured into water. The mixture is extracted with ethyl acetate and the organic phase is washed 3× with water. The organic solution is dried over sodium sulfate and the solvent is removed under reduced pressure. The residual dark oil is purified by flash chromatography using methylene chloride to elute the product as a dark oil. This is used directly in the next step.

Aufarbeitung

  1. additionis added
  2. stirringthe mixture is stirred at 60° C. for 2 h
  3. customis nearly consumed
  4. temperatureto cool
  5. additionthen is poured into water
  6. extractionThe mixture is extracted with ethyl acetate
  7. washthe organic phase is washed 3× with water
  8. dry with materialThe organic solution is dried over sodium sulfate
  9. customthe solvent is removed under reduced pressure
  10. customThe residual dark oil is purified by flash chromatography
  11. washto elute the product as a dark oil

Quellen und Nachweise

ORD-Eintrag
ord-ddde81f4844044b7b1dd97e59431e00c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252820B2

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