Water → HCID 59635660, Verbindung

HRID 406768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406768
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5]Br.[Br:10][C:11]1[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][N:14]1[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][C:13]1=[O:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8171154-Bromo-2-hydroxypyridineHCID 19604604methyl 3-bromo-2,2-dimethylpropanoate

Produkt 1

HCID 59635660HCID 59635660, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-Bromo-2,2-dimethyl-propionic acid methyl ester (0.75 g) was added to a mixture of 4-bromo-1H-pyridin-2-one (0.55 g) and potassium carbonate (0.75 g) in N,N-dimethylformamide (10 mL) at room temperature. The mixture was heated to 60° C. and stirred at this temperature overnight. After stirring at 80° C. for another 8 h, the mixture was cooled to room temperature and water was added. The resultant mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1) to afford the title compound; 3-(4-bromo-pyridin-2-yloxy)-2,2-dimethyl-propionic acid methyl ester (0.35 g) was also obtained from this reaction. Yield: 0.29 g (32% of theory); Mass spectrum (ESI+): m/z=288/300 (Br) [M+H]+.

Aufarbeitung

  1. stirringAfter stirring at 80° C. for another 8 h
  2. temperaturethe mixture was cooled to room temperature
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-546038c01ef1422693c610f5503dc413
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754076B2

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