Реакция #1552055

Уравнение реакции

p-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

objective light brown plate-shaped crystal

Выход 36.2%

9-(4-bromophenyl)carbazole

Выход 36.2%

Растворители

N,N′-dimethylpropyleneurea

Условия реакции

Обработка

1. 1
   ТемператураAfter the reaction mixture was cooled to room temperature
2. 2
   Другоеa precipitate was removed by suction filtration
3. 3
   ПромывкаThe filtrate washed with dilute hydrochloric acid
4. 4
   Сушкаa saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in this order and dried with magnesium sulfate
5. 5
   ДругоеAfter being dried
6. 6
   Фильтрацияthe solution was filtered naturally
7. 7
   Другоеcondensed
8. 8
   Другоеan obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
9. 9
   Другоеrecrystallized with chloroform and hexane

Методика

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%).

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