反応 #1552055

反応方程式

p-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

objective light brown plate-shaped crystal

収率 36.2%

9-(4-bromophenyl)carbazole

収率 36.2%

溶媒

N,N′-dimethylpropyleneurea

反応条件

後処理

1. 1
   温度After the reaction mixture was cooled to room temperature
2. 2
   その他a precipitate was removed by suction filtration
3. 3
   洗浄The filtrate washed with dilute hydrochloric acid
4. 4
   乾燥a saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in this order and dried with magnesium sulfate
5. 5
   その他After being dried
6. 6
   ろ過the solution was filtered naturally
7. 7
   その他condensed
8. 8
   その他an obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
9. 9
   その他recrystallized with chloroform and hexane

実験手順

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%).

出典