2-Benzyloxy-5-nitroiodobenzene → 4-(Benzyloxy)-3-iodobenzenamine

HRID 842039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842039
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[I:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.C(O)(=O)C.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[I:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 1

HCID 226181932-Benzyloxy-5-nitroiodobenzene

Produkt 1

HCID 226181994-(Benzyloxy)-3-iodobenzenamineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-80 °C

Versuchsvorschrift

Iron powder (12.5 g, 224 mmol) was added to a suspension of 2-benzyloxy-5-nitroiodobenzene (10 g, 28 mmol) in water (300 ml) and acetic acid (75 ml) and the mixture was stirred at −80° C. for 12 hours. The mixture was allowed to cool to room temperature and filtered through Hyflo™, washing with 4:1 water:acetic acid and ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic extract was evaporated under reduced pressure. Saturated aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4), and the solvent was evaporated under reduced pressure to give the title compound as a brown oil (9 g, 99% yield). 1H NMR (360 MHz, CDCl3) δ 7.49-7.47 (2H, m), 7.40-7.28 (3H, m), 7.19 (1H, d, J 2.4 Hz), 6.70 (1H, d, J 8.6 Hz), 6.62 (1H, dd, J 2.4, 8.6 Hz), 5.04 (2H, s). MS (ES+) m/z 326 (M+H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Hyflo™
  3. washwashing with 4:1 water
  4. extractionThe filtrate was extracted with ethyl acetate
  5. extractionthe organic extract
  6. customwas evaporated under reduced pressure
  7. additionSaturated aqueous sodium hydrogen carbonate was added
  8. extractionthe mixture was extracted with ethyl acetate
  9. extractionThe organic extract
  10. washwas washed with brine
  11. dry with materialdried (MgSO4)
  12. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8d020c5621e64f8eb6ea154f6134c514
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372754B1

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