Reacción #1447078

Ecuación de reacción

1,4-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

N-(4-bromophenyl)carbazole

Rendimiento 35.0%

Disolventes

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturaThe reactive mixture was cooled to a room temperature
3. 3
   Otroa precipitate was removed by suction filtration
4. 4
   LavadoThen, the filtrate was washed with diluted hydrochloric acid
5. 5
   SecadoAfter the washing, the filtrate was dried with magnesium sulfate
6. 6
   FiltraciónAfter the drying, the reactive mixture was naturally filtrated
7. 7
   FiltraciónAfter the filtration
8. 8
   Concentraciónthe filtrate was concentrated
9. 9
   OtroThen, the thus-obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
10. 10
    Otroit was recrystallized by chloroform and hexane
11. 11
    Otrowas obtained

Procedimiento

First, 56.3 g (0.24 mol) of 1,4-dibromobenzene, 31.3 g (0.18 mol) of carbazole, 4.6 g (0.024 mol) of copper iodide, 66.3 g (0.48 mol) of potassium carbonate, and 2.1 g (0.008 mol) of 18-crown-6-ether were put in a three-neck flask of 300 mL. After nitrogen was substituted for air in the three-neck flask, 8 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was added thereto, and the mixture was stirred at 180° C. for 6 hours. The reactive mixture was cooled to a room temperature, and then a precipitate was removed by suction filtration. Then, the filtrate was washed with diluted hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution, and saturated saline in this order. After the washing, the filtrate was dried with magnesium sulfate. After the drying, the reactive mixture was naturally filtrated. After the filtration, the filtrate was concentrated. Then, the thus-obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), and thereafter, it was recrystallized by chloroform and hexane. Thus, 20.7 g (yield: 35%) of a light brown plate crystal, which was target matter, was obtained.

Fuente