Реакция #155317

Уравнение реакции

7-bromo-5-methylbenzofuran

benzophenone imine

sodium t-butoxide

ammonium chloride

→

benzhydrylidene(5-methylbenzofuran-7-yl) amine

Выход 125.0%

Растворители

water

Условия реакции

Обработка

1. 1
   Температураwhile heating
2. 2
   Температураunder reflux in a nitrogen atmosphere
3. 3
   Экстракцияfollowed by extraction
4. 4
   СушкаThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Концентрированиеconcentrated to dryness under reduced pressure
6. 6
   ДругоеThe residue was purified
7. 7
   ДругоеThe solvent was removed under a reduced pressure

Методика

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%).

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