Bromine → 2-Benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acid

HRID 569363

Reaktionsgleichung

Reaktionsgleichung von HRID 569363
[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:22](=[O:24])[CH3:23])[C:15]([O:17]C(C)(C)C)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]Br>C(O)(=O)C>[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:22](=[O:24])[CH2:23][Br:25])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 53811665Tert-butyl 2-benzyloxycarbonylmethoxyimino-3-oxobutyrate

Produkt 1

HCID 540321592-Benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acidAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-benzyloxycarbonylmethoxyimino-3-oxobutyrate (32.3 g) in acetic acid (32 ml) was slowly added bromine (16 g) at 45° to 48° C. with stirring, and the stirring was continued at the same temperature for 30 minutes. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, followed by washing six times with a saturated aqueous sodium chloride. This solution was evaporated under reduced pressure to give 2-benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acid (35 g).

Aufarbeitung

  1. customat 45° to 48° C.
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washby washing six times with a saturated aqueous sodium chloride
  5. customThis solution was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eef14ec9e3334d10bd07feeb57874447
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731443

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