Bromine → 5-Bromo-3-(tert-butyl)-2-hydroxybenzaldehyde

HRID 1296019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296019
[Br:1]Br.[C:3]([C:7]1[C:8]([O:15]COC)=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])([CH3:6])([CH3:5])[CH3:4]>CO>[Br:1][C:13]1[CH:14]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:8]([OH:15])=[C:9]([CH:12]=1)[CH:10]=[O:11]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 22930050HCID 22930050, Verbindung

Produkt 1

HCID 7970065-Bromo-3-(tert-butyl)-2-hydroxybenzaldehydeAusbeute 111 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Bromine (747 g) was gradually added to a solution of the 3-(tert-butyl)-2-(methoxymethoxy)benzaldehyde (1247 g, 4.67 mol) in methanol (4000 ml) while cooling on ice. After stirring at 20° C. for 1 hour, the solvent was distilled off under reduced pressure, ethyl acetate was added to the residue, the mixture was washed with water, saturated sodium aqueous hydrogencarbonate and brine in that order and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to yield a crude product of the title compound (1333 g) as a red oil.

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. distillationthe solvent was distilled off under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. washthe mixture was washed with water, saturated sodium aqueous hydrogencarbonate and brine in that order
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3b9cde35ea9f4b3fb439de6be3084343
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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