反应 #155317

反应方程式

7-bromo-5-methylbenzofuran

benzophenone imine

sodium t-butoxide

ammonium chloride

→

benzhydrylidene(5-methylbenzofuran-7-yl) amine

收率 125.0%

溶剂

water

反应条件

后处理

1. 1
   温度while heating
2. 2
   温度under reflux in a nitrogen atmosphere
3. 3
   萃取followed by extraction
4. 4
   干燥The organic layer was dried over anhydrous magnesium sulfate
5. 5
   浓缩concentrated to dryness under reduced pressure
6. 6
   其他The residue was purified
7. 7
   其他The solvent was removed under a reduced pressure

实验过程

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%).

来源