반응 #70062

반응 방정식

p-dibromobenzene

9H-carbazole

potassium carbonate

18-crown-6-ether

→

9-(4-bromophenyl)-9H-carbazole

수율 35.0%

용매

toluene

N,N′-dimethylpropyleneurea

반응 조건

후처리

1. 1
   온도After the stirring, the mixture was cooled to 100° C
2. 2
   온도the mixture was cooled to room temperature
3. 3
   여과After the cooling, this mixture was subjected to suction filtration so that the precipitate
4. 4
   기타was removed
5. 5
   세척The obtained filtrate was washed with dilute hydrochloric acid
6. 6
   건조The organic layer was dried with magnesium sulfate
7. 7
   여과Then, the mixture was subjected to gravity filtration
8. 8
   기타condensed
9. 9
   기타to give an oily substance
10. 10
    기타This oily substance was purified by silica gel column chromatography (a developing solvent
11. 11
    기타ether acetate=9:1), and then recrystallized with chloroform/hexane
12. 12
    기타to give 21 g of a light brown plate-like crystal, which
13. 13
    기타the object of the synthesis
14. 14
    기타A synthesis scheme of Step 1

실험 절차

56 g (240 mmol) of p-dibromobenzene, 31 g (180 mmol) of 9H-carbazole, 4.6 g (24 mmol) of copper(I) iodide, 66 g (480 mmol) of potassium carbonate, and 2.1 g (8 mmol) of 18-crown-6-ether were put into a 300 mL three-neck flask. The mixture was heated at about 100° C., and then 8 mL of N,N′-dimethylpropyleneurea (DMPU) was added thereto. This mixture was stirred at 180° C. for 6 hours. After the stirring, the mixture was cooled to 100° C. To the mixture was added about 200 mL of toluene, and then the mixture was cooled to room temperature. After the cooling, this mixture was subjected to suction filtration so that the precipitate was removed. The obtained filtrate was washed with dilute hydrochloric acid, a saturated sodium hydrogen carbonate solution, and a saturated saline solution in this order. The organic layer was dried with magnesium sulfate. Then, the mixture was subjected to gravity filtration. The obtained filtrate was condensed to give an oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was a mixed solvent of hexane:ether acetate=9:1), and then recrystallized with chloroform/hexane to give 21 g of a light brown plate-like crystal, which was the object of the synthesis, at a yield of 35%. A synthesis scheme of Step 1 is shown in (f-1) given below.

출처