تفاعل #1447078

معادلة التفاعل

1,4-dibromobenzene

carbazole

potassium carbonate

18-crown-6-ether

→

N-(4-bromophenyl)carbazole

المردود 35.0%

المذيبات

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

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةThe reactive mixture was cooled to a room temperature
3. 3
   أخرىa precipitate was removed by suction filtration
4. 4
   غسيلThen, the filtrate was washed with diluted hydrochloric acid
5. 5
   تجفيفAfter the washing, the filtrate was dried with magnesium sulfate
6. 6
   ترشيحAfter the drying, the reactive mixture was naturally filtrated
7. 7
   ترشيحAfter the filtration
8. 8
   تركيزthe filtrate was concentrated
9. 9
   أخرىThen, the thus-obtained oily substance was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
10. 10
    أخرىit was recrystallized by chloroform and hexane
11. 11
    أخرىwas obtained

الإجراء التجريبي

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.

المصدر