Tetrahydrofuran → 2-Nitro-4-(pentafluoroethyl)benzaldehyde

HRID 1689726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689726
CN(C)/C=[CH:4]/[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].C1C[O:25]CC1>P([O-])([O-])([O-])=O>[N+:18]([C:6]1[CH:7]=[C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:25])([O-:20])=[O:19]

Komponenten

4

Edukt 2

HCID 8028TetrahydrofuranHCID 86623311HCID 86623311, Verbindung

Produkt 1

HCID 573559322-Nitro-4-(pentafluoroethyl)benzaldehydeAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1061PhosphateLösungsmittel

Versuchsvorschrift

To a solution of crude (E)-N,N-dimethyl-2-(2-nitro-4-(perfluoroethyl)phenyl)ethenamine (12.2 g, 39.2 mmol) in THF (300 mL) and pH 7.2 phosphate buffer (300 mL) was added NaIO4 (29.3 g, 137.2 mmol). After 2.5 hours an aliquot (˜0.3 mL) was removed, filtered and dried. The proton NMR of this sample indicated that the reaction was complete. The solids were removed and the filter cake was washed with EtOAc. The filtrate was washed with brine (2×100 mL), dried and concentrated. The concentrate was purified via flash chromatography (100% hexane to 5% EtOAc) to provide 2-nitro-4-(perfluoroethyl)benzaldehyde (5.4 g, 52%).

Aufarbeitung

  1. customAfter 2.5 hours an aliquot (˜0.3 mL) was removed
  2. filtrationfiltered
  3. customdried
  4. customThe solids were removed
  5. washthe filter cake was washed with EtOAc
  6. washThe filtrate was washed with brine (2×100 mL)
  7. customdried
  8. concentrationconcentrated
  9. customThe concentrate was purified via flash chromatography (100% hexane to 5% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e5c74aed5e6d485980e45209a3e3327d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153622B2

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