Reacción #155317

Ecuación de reacción

7-bromo-5-methylbenzofuran

benzophenone imine

sodium t-butoxide

ammonium chloride

→

benzhydrylidene(5-methylbenzofuran-7-yl) amine

Rendimiento 125.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile heating
2. 2
   Temperaturaunder reflux in a nitrogen atmosphere
3. 3
   Extracciónfollowed by extraction
4. 4
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated to dryness under reduced pressure
6. 6
   OtroThe residue was purified
7. 7
   OtroThe solvent was removed under a reduced pressure

Procedimiento

To a 7-bromo-5-methylbenzofuran (9.71 g, 46 mmol) toluene solution (100 ml) were added a benzophenone imine (10.25 g, 56 mmol) toluene solution (55 ml), tris(dibenzylideneacetone)dipalladium (1.1 g, 1 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 2.1 g, 3.45 mmol), and sodium t-butoxide (3.1 g, 31 mmol). The resulting mixture was then stirred for 4 hours while heating under reflux in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and water and saturated ammonium chloride solution were added thereto, followed by extraction using ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to dryness under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=10:1). The solvent was removed under a reduced pressure, giving a yellow oily substance of benzhydrylidene(5-methylbenzofuran-7-yl) amine (17.9 g, yield: 81%).

Fuente