Dichloromethane → 6-Bromo-5-methoxypicolinaldehyde

HRID 488815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488815
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH3:10])[N:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:12].[K+].[K+].C(Cl)Cl>C(#N)C.O>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([CH:10]=[O:12])=[N:3][C:2]=1[Br:1]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 24412Potassium PersulfateHCID 109655632-Bromo-3-methoxy-6-methylpyridine

Produkt 1

HCID 222683396-Bromo-5-methoxypicolinaldehydeAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

A stirred mixture of 2-bromo-3-methoxy-6-methyl-pyridine (2.00 g, 9.9 mmol), Cu(II) sulfate pentahydrate (2.47 g, 9.9 mmol), and potassium peroxydisulfate (8.03 g, 29.7 mmol) in 80 mL of acetonitrile/H2O (1:1) was heated under reflux. After 1 hour, the dark green mixture was cooled to room temperature and CH2Cl2 was added. The layers were separated and the aqueous layer further extracted with CH2Cl2. The organics were combined, dried (MgSO4), filtered and evaporated. The resulting crude product was purified on silica gel [Biotage, hexane:ethyl acetate (4:1)] to give a white solid (0.51 g, 24% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe layers were separated
  4. extractionthe aqueous layer further extracted with CH2Cl2
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting crude product was purified on silica gel [Biotage, hexane:ethyl acetate (4:1)]

Quellen und Nachweise

ORD-Eintrag
ord-d064aa9791fb4b8394ad183c1d577c0c
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974826B2

Notizen zur Reaktion

Wird geladen…