반응 #1447078

반응 방정식

1,4-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

N-(4-bromophenyl)carbazole

수율 35.0%

용매

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

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도The reactive mixture was cooled to a room temperature
3. 3
   기타a precipitate was removed by suction filtration
4. 4
   세척Then, the filtrate was washed with diluted hydrochloric acid
5. 5
   건조After the washing, the filtrate was dried with magnesium sulfate
6. 6
   여과After the drying, the reactive mixture was naturally filtrated
7. 7
   여과After the filtration
8. 8
   농축the filtrate was concentrated
9. 9
   기타Then, the thus-obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
10. 10
    기타it was recrystallized by chloroform and hexane
11. 11
    기타was obtained

실험 절차

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.

출처