反応 #1447078

反応方程式

1,4-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

N-(4-bromophenyl)carbazole

収率 35.0%

溶媒

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

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度The reactive mixture was cooled to a room temperature
3. 3
   その他a precipitate was removed by suction filtration
4. 4
   洗浄Then, the filtrate was washed with diluted hydrochloric acid
5. 5
   乾燥After the washing, the filtrate was dried with magnesium sulfate
6. 6
   ろ過After the drying, the reactive mixture was naturally filtrated
7. 7
   ろ過After the filtration
8. 8
   濃縮the filtrate was concentrated
9. 9
   その他Then, the thus-obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
10. 10
    その他it was recrystallized by chloroform and hexane
11. 11
    その他was obtained

実験手順

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.

出典