Reaktion #1447078

Reaktionsgleichung

1,4-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

N-(4-bromophenyl)carbazole

Ausbeute 35.0%

Lösungsmittel

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturThe reactive mixture was cooled to a room temperature
3. 3
   Sonstigea precipitate was removed by suction filtration
4. 4
   WaschenThen, the filtrate was washed with diluted hydrochloric acid
5. 5
   TrocknenAfter 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
   Einengenthe filtrate was concentrated
9. 9
   SonstigeThen, the thus-obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
10. 10
    Sonstigeit was recrystallized by chloroform and hexane
11. 11
    Sonstigewas obtained

Vorschrift

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.

Quelle