Reacción #1605825

ord-8f28a22d5869481eb977534dd657f48a

Ecuación de reacción

O=C(O)c1ccc(Br)c([N+](=O)[O-])c1
4-Bromo-3-nitrobenzoic acid
OB(O)Oc1ccccc1
phenyl boric acid
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
O=C(O)c1ccc(-c2ccccc2)c([N+](=O)[O-])c1
3-nitro-4-phenylbenzoic acid

Disolventes

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otropurified water (10 mL)
  2. 2
    FiltraciónThe reaction solution was filtered through celite, alumina, and Florisil
  3. 3
    Extracciónwas extracted with ethyl acetate
  4. 4
    LavadoThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. 5
    Secadodried over anhydrous magnesium sulfate
  6. 6
    Concentraciónconcentrated under reduced pressure

Procedimiento

4-Bromo-3-nitrobenzoic acid (1.0 g, 2.5 mmol) was dissolved in 1,4-dioxane (30 mL), and, thereto were added phenyl boric acid (610 mg, 5.0 mmol), cesium carbonate (6.5 g, 20.0 mmol), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (204 mg, 0.10 mmol), and purified water (10 mL). The reaction mixture was stirred under a nitrogen flow at 80° C. overnight. The reaction solution was filtered through celite, alumina, and Florisil, and, thereafter, was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3-nitro-4-phenylbenzoic acid as a crude material.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09072734B2uspto-grants-2015_07