반응 #1552055

반응 방정식

p-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

objective light brown plate-shaped crystal

수율 36.2%

9-(4-bromophenyl)carbazole

수율 36.2%

용매

N,N′-dimethylpropyleneurea

반응 조건

후처리

1. 1
   온도After the reaction mixture was cooled to room temperature
2. 2
   기타a precipitate was removed by suction filtration
3. 3
   세척The filtrate washed with dilute hydrochloric acid
4. 4
   건조a saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in this order and dried with magnesium sulfate
5. 5
   기타After being dried
6. 6
   여과the solution was filtered naturally
7. 7
   기타condensed
8. 8
   기타an obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
9. 9
   기타recrystallized with chloroform and hexane

실험 절차

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%).

출처