Réaction #1605804

Équation de réaction

3-(4-Bromo-3-nitrobenzoyl)propionic acid

phenyl boric acid

cesium carbonate

→

3-(3-nitro-4-phenylbenzoyl)propionic acid

Rendement 87.8%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Autrepurified water (150 mL)
2. 2
   FiltrationThe reaction solution was filtered through celite, alumina, and Florisil
3. 3
   Autrethe aqueous layer was separated
4. 4
   ExtractionThe organic layer was extracted with a dilute aqueous solution of sodium hydroxide
5. 5
   Lavagewashed with ethyl acetate
6. 6
   Extractionextracted with ethyl acetate
7. 7
   LavageThe organic layer was washed with a saturated aqueous solution of sodium chloride
8. 8
   Séchagedried over anhydrous magnesium sulfate
9. 9
   Concentrationconcentrated under reduced pressure

Mode opératoire

3-(4-Bromo-3-nitrobenzoyl)propionic acid (45.3 g, 150.0 mmol) was dissolved in 1,4-dioxane (400 mL), thereto were added phenyl boric acid (27.4 g, 225.0 mmol), cesium carbonate (146.6 g, 450.0 mmol), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (3.7 g, 4.5 mmol), and purified water (150 mL), and 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, the aqueous layer was separated. The organic layer was extracted with a dilute aqueous solution of sodium hydroxide. After the aqueous layers were combined and washed with ethyl acetate, the layer was acidified, under ice-water cooling, with 6 M hydrochloric acid and 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-(3-nitro-4-phenylbenzoyl)propionic acid (39.4 g).

Source