Reaktion #417970

ord-de26211d84ef4f39a152704ee6299ee7

Reaktionsgleichung

CC(=O)O
Acetic acid
O=[N+]([O-])c1ccc(Br)c(OCCOc2ccccc2)c1
25b
O=[N+]([O-])c1ccc(Br)c(OCCOc2ccccc2)c1
1-bromo-4-nitro-2-(2-phenoxy-ethoxy)-benzene
Nc1ccc(Br)c(OCCOc2ccccc2)c1
aniline
Ausbeute 84.0%
Nc1ccc(Br)c(OCCOc2ccccc2)c1
4-bromo-3-(2-phenoxy-ethoxy)-phenylamine
Ausbeute 84.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe mixture was filtered
  2. 2
    workup.DISTILLATIONthe solvent distilled off under reduced pressure
  3. 3
    Sonstigethe crude was purified by flash column chromatography

Vorschrift

Acetic acid (1.068 mL, 18 mmol) was added to the mixture of 25b (600 mg, 1.8 mmol) and zinc dust (1.157 g, 18.0 mmol) in ethanol (10 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 4 hrs. The mixture was filtered, the solvent distilled off under reduced pressure and the crude was purified by flash column chromatography to obtain the aniline 25c in 84% yield.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877752B2uspto-grants-2014_11