Réaction #1447078

Équation de réaction

1,4-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

N-(4-bromophenyl)carbazole

Rendement 35.0%

Solvants

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

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThe reactive mixture was cooled to a room temperature
3. 3
   Autrea precipitate was removed by suction filtration
4. 4
   LavageThen, the filtrate was washed with diluted hydrochloric acid
5. 5
   SéchageAfter the washing, the filtrate was dried with magnesium sulfate
6. 6
   FiltrationAfter the drying, the reactive mixture was naturally filtrated
7. 7
   FiltrationAfter the filtration
8. 8
   Concentrationthe filtrate was concentrated
9. 9
   AutreThen, the thus-obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
10. 10
    Autreit was recrystallized by chloroform and hexane
11. 11
    Autrewas obtained

Mode opératoire

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.

Source