Water → 5-Bromo-2-(oxiran-2-ylmethoxy)benzaldehyde

HRID 38982

Reaktionsgleichung

Reaktionsgleichung von HRID 38982
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([CH:13]1[O:15][CH2:14]1)Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:13]2[CH2:14][O:15]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 728635-Bromosalicylaldehyde

Produkt 1

HCID 212209825-Bromo-2-(oxiran-2-ylmethoxy)benzaldehydeAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 5-bromo-2-hydroxybenzaldehyde (10 g, 50 mmol), epibromohydrin (13.6 g, 100 mmol) and K2CO3 (10.3 g, 75 mmol) in DMF (50 ml) was heated at 60° C. for 2 h. The mixture was cooled to ambient temperature and water and EtOAc was added. The phases were separated and the combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (12.3 g). MS m/z (rel. intensity, 70 eV) 256 (M+, 41), 201 (77), 200 (bp), 199 (84), 63 (60).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe phases were separated
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (isooctane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a41bf53d783d4cf782501d10381e2b84
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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