Sodium Bicarbonate → 2-Bromo-5-(dimethoxymethyl)pyridine

HRID 1281143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281143
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.O.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:22](=[O:25])(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:25][CH3:22])[O:9][CH3:11])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Produkt 1

HCID 64252132-Bromo-5-(dimethoxymethyl)pyridineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-5-pyridinecarboxaldehyde (1.02 g, 5.48 mmol) in methanol (100 mL) was added p-toluenesulfonic acid hydrate (1.05 g, 5.53 mmol), and the mixture was heated at reflux for 1.5 h. Diluted aqueous sodium bicarbonate was added, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 2-bromo-5-dimethoxymethylpyridine (1.19 g, 94%) as an oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c9b2444ae6742508796e48be196f153
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06452014B1

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