Réaction #1605815

Équation de réaction

1-Bromo-4-methoxy-2-nitrobenzene

phenyl boric acid

cesium carbonate

→

4-methoxy-2-nitro-1-phenylbenzene

Rendement 81.1%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Autrepurified water (12 mL)
2. 2
   FiltrationThe reaction solution was filtered through celite, alumina, and Florisil
3. 3
   Extractionextracted with ethyl acetate
4. 4
   LavageThe organic layer was washed with a saturated aqueous solution of sodium chloride
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by flash column chromatography

Mode opératoire

1-Bromo-4-methoxy-2-nitrobenzene (2.32 g, 10 mmol) was dissolved in 1,4-dioxane (30 mL) and, thereto, were added phenyl boric acid (2.44 g, 20 mmol), cesium carbonate (26 g, 80 mmol), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.82 g, 1 mmol), and purified water (12 mL). The reaction mixture was stirred under a nitrogen flow at 80° C. for 18 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 4-methoxy-2-nitro-1-phenylbenzene (1.86 g).

Source