تفاعل #155317

معادلة التفاعل

7-bromo-5-methylbenzofuran

benzophenone imine

sodium t-butoxide

ammonium chloride

→

benzhydrylidene(5-methylbenzofuran-7-yl) amine

المردود 125.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile heating
2. 2
   درجة الحرارةunder reflux in a nitrogen atmosphere
3. 3
   استخلاصfollowed by extraction
4. 4
   تجفيفThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   تركيزconcentrated to dryness under reduced pressure
6. 6
   أخرىThe residue was purified
7. 7
   أخرىThe solvent was removed under a reduced pressure

الإجراء التجريبي

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%).

المصدر