Dimethyl Sulfate → 2-Bromo-3,4-dimethoxybenzaldehyde

HRID 1582381

Reaktionsgleichung

Reaktionsgleichung von HRID 1582381
[Br:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O>CN(C=O)C>[Br:1][C:2]1[C:9]([O:10][CH3:13])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2240112-Bromoisovanillin

Produkt 1

HCID 6185382-Bromo-3,4-dimethoxybenzaldehydeAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A stirred suspension of 2-bromo-3-hydroxy-4-methoxybenzaldehyde (commercially available, 24 g, 104 mmol) and K2CO3 (29.4 g, 213 mmol) in DMF (125 ml) was cooled to −10° C. Dimethylsulfate (9.6 ml, 102 mmol) was added, the reaction was warmed to room temperature and stirred overnight. The resulting solution was quenched with water (375 ml) and the resulting suspension stirred overnight. The resulting suspension was filtered and the solid dried in vacuo at 50° C. to give 23.1 g of the subtitle product (91%).

Aufarbeitung

  1. temperaturethe reaction was warmed to room temperature
  2. customThe resulting solution was quenched with water (375 ml)
  3. stirringthe resulting suspension stirred overnight
  4. filtrationThe resulting suspension was filtered
  5. customthe solid dried in vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-77781cbf596048309d1391566e70b02b
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734303B2

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