Reacción #1605800

Ecuación de reacción

tert-Butyl trans-3-(4-bromo-3-nitrophenyl)acrylate

phenyl boric acid

cesium carbonate

→

tert-butyl trans-3-(3-nitro-4-phenylphenyl)acrylate

Rendimiento 93.2%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropurified water (50 mL)
2. 2
   FiltraciónThe reaction solution was filtered through celite, alumina, and Florisil
3. 3
   Extracciónextracted 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
7. 7
   OtroThe residue was purified by flash column chromatography

Procedimiento

tert-Butyl trans-3-(4-bromo-3-nitrophenyl)acrylate (7.07 g, 21.5 mmol) was dissolved in 1,4-dioxane (200 mL) and thereto were added phenyl boric acid (5.25 g, 42.1 mmol), cesium carbonate (56.1 g, 172.2 mmol), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.88 g, 1.1 mmol), and purified water (50 mL). The mixture was stirred under a nitrogen flow at 80° C. for 4 hours. The reaction solution was filtered through celite, alumina, and Florisil, and, thereafter, 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. The residue was purified by flash column chromatography to obtain tert-butyl trans-3-(3-nitro-4-phenylphenyl)acrylate (6.52 g).

Fuente