Реакция #70062

Уравнение реакции

p-dibromobenzene

9H-carbazole

potassium carbonate

18-crown-6-ether

→

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

Выход 35.0%

Растворители

toluene

N,N′-dimethylpropyleneurea

Условия реакции

Обработка

1. 1
   ТемператураAfter the stirring, the mixture was cooled to 100° C
2. 2
   Температураthe mixture was cooled to room temperature
3. 3
   ФильтрацияAfter the cooling, this mixture was subjected to suction filtration so that the precipitate
4. 4
   Другоеwas removed
5. 5
   ПромывкаThe obtained filtrate was washed with dilute hydrochloric acid
6. 6
   СушкаThe organic layer was dried with magnesium sulfate
7. 7
   ФильтрацияThen, the mixture was subjected to gravity filtration
8. 8
   Другоеcondensed
9. 9
   Другоеto give an oily substance
10. 10
    ДругоеThis oily substance was purified by silica gel column chromatography (a developing solvent
11. 11
    Другоеether acetate=9:1), and then recrystallized with chloroform/hexane
12. 12
    Другоеto give 21 g of a light brown plate-like crystal, which
13. 13
    Другоеthe object of the synthesis
14. 14
    ДругоеA synthesis scheme of Step 1

Методика

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.

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