(E)-1-(4-bromo-2-nitrostyryl)pyrrolidine → 4-Bromo-2-nitrobenzaldehyde

HRID 37982

Reaktionsgleichung

Reaktionsgleichung von HRID 37982
I([O-])(=O)(=O)=[O:2].[Na+].[Br:7][C:8]1[CH:20]=[CH:19][C:11](/[CH:12]=C/N2CCCC2)=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1>C1COCC1.O>[Br:7][C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[O:2])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1

Komponenten

4

Edukt 2

HCID 10913500(E)-1-(4-bromo-2-nitrostyryl)pyrrolidineHCID 23667635Sodium periodate

Produkt 1

HCID 6080994-Bromo-2-nitrobenzaldehydeAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of sodium periodate (298 g, 1.40 mol) in THF—H2O (4 L, 1:1) at 0° C. was added (E)-1-(4-bromo-2-nitrostyryl)pyrrolidine (138 g, 464 mmol). The mixture was stirred for 15 h and then filtered to remove solid precipitates. The aqueous layer from the filtrate was separated and extracted with EtOAc (4×200 mL). The combined organic layers were washed with H2O (2×200 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude product that was purified by silica gel flash column chromatography (5% EtOAc in hexanes) to afford 91 g (86%) of 4-bromo-2-nitrobenzaldehyde.

Aufarbeitung

  1. filtrationfiltered
  2. customto remove solid
  3. customprecipitates
  4. customThe aqueous layer from the filtrate was separated
  5. extractionextracted with EtOAc (4×200 mL)
  6. washThe combined organic layers were washed with H2O (2×200 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give the crude product that
  11. customwas purified by silica gel flash column chromatography (5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7c58f615c7d14710be3b75f9a1001369
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524702B2

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