Reaktion #1552055

Reaktionsgleichung

p-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

objective light brown plate-shaped crystal

Ausbeute 36.2%

9-(4-bromophenyl)carbazole

Ausbeute 36.2%

Lösungsmittel

N,N′-dimethylpropyleneurea

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter the reaction mixture was cooled to room temperature
2. 2
   Sonstigea precipitate was removed by suction filtration
3. 3
   WaschenThe filtrate washed with dilute hydrochloric acid
4. 4
   Trocknena saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in this order and dried with magnesium sulfate
5. 5
   SonstigeAfter being dried
6. 6
   Filtrationthe solution was filtered naturally
7. 7
   Sonstigecondensed
8. 8
   Sonstigean obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
9. 9
   Sonstigerecrystallized with chloroform and hexane

Vorschrift

First, 56 g (240 mmol) of p-dibromobenzene, 31 g (180 mmol) of carbazole, 4.6 g (24 mmol) of copper iodide, 66 g (480 mmol) of potassium carbonate, and 2.1 g (8 mmol) of 18-crown-6-ether were put in a 300-mL three-neck flask, and nitrogen was substituted for air in the flask. Then, 8 mL of N,N′-dimethylpropyleneurea (abbreviation: DMPU) was added therein, and the mixture was stirred at 180° C. for 6 hours. After the reaction mixture was cooled to room temperature, a precipitate was removed by suction filtration. The filtrate washed with dilute hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in this order and dried with magnesium sulfate. After being dried, the solution was filtered naturally and condensed, and an obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) and recrystallized with chloroform and hexane; thus, 21 g of an objective light brown plate-shaped crystal of 9-(4-bromophenyl)carbazole was obtained (yield: 35%).

Quelle