Reacción #417970

ord-de26211d84ef4f39a152704ee6299ee7

Ecuación de reacción

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
Rendimiento 84.0%
Nc1ccc(Br)c(OCCOc2ccccc2)c1
4-bromo-3-(2-phenoxy-ethoxy)-phenylamine
Rendimiento 84.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08877752B2uspto-grants-2014_11