Reaction #1552055

Reaction equation

p-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

objective light brown plate-shaped crystal

Yield 36.2%

9-(4-bromophenyl)carbazole

Yield 36.2%

Solvents

N,N′-dimethylpropyleneurea

Conditions

Workup

1. 1
   TemperatureAfter the reaction mixture was cooled to room temperature
2. 2
   Othera precipitate was removed by suction filtration
3. 3
   WashThe filtrate washed with dilute hydrochloric acid
4. 4
   Dryinga saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in this order and dried with magnesium sulfate
5. 5
   OtherAfter being dried
6. 6
   Filtrationthe solution was filtered naturally
7. 7
   Othercondensed
8. 8
   Otheran obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
9. 9
   Otherrecrystallized with chloroform and hexane

Procedure

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%).

Source