Reaktion #155317

Reaktionsgleichung

7-bromo-5-methylbenzofuran

benzophenone imine

sodium t-butoxide

ammonium chloride

→

benzhydrylidene(5-methylbenzofuran-7-yl) amine

Ausbeute 125.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile heating
2. 2
   Temperaturunder reflux in a nitrogen atmosphere
3. 3
   Extraktionfollowed by extraction
4. 4
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated to dryness under reduced pressure
6. 6
   SonstigeThe residue was purified
7. 7
   SonstigeThe solvent was removed under a reduced pressure

Vorschrift

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%).

Quelle