Dichloromethane → 6-Bromo-5-methoxypicolinaldehyde

HRID 1057833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057833
[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-833df49558c141e0a2b203b940cc3eb3
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515003B1

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