m-Chloroperbenzoic acid → 5-Bromo-2-(oxiran-2-ylmethoxy)phenyl formate

HRID 38983

Reaktionsgleichung

Reaktionsgleichung von HRID 38983
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)=[C:6]([CH:9]=1)C=O.C1C=C(Cl)C=C([C:22]([O:24]O)=[O:23])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:22]([O:24][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][CH:12]1[CH2:14][O:13]1)=[O:23]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 212209825-Bromo-2-(oxiran-2-ylmethoxy)benzaldehyde

Produkt 1

HCID 212210275-Bromo-2-(oxiran-2-ylmethoxy)phenyl formate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-bromo-2-(oxiran-2-ylmethoxy)benzaldehyde (12.3 g, 47.7 mmol) in DCM (50 ml) was added m-CPBA (12.8 g, 57.2 mmol). The solution was heated at reflux for 3 h and 30 min and then brought to ambient temperature. Aqueous sodium bicarbonate (saturated) and DCM was added and the phases were separated. The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness to give the crude title compound. Crude yield: 12.3 g. MS m/z (rel. intensity, 70 eV) 272 (M+, 7), 244 (50), 189 (95), 188 (bp), 57 (93).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 h and 30 min
  3. custombrought to ambient temperature
  4. customthe phases were separated
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-767b3078aa2d471d93d3027cc3832986
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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