Carbazole → 9H-3,9'-Bicarbazole

HRID 2045742노트

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HRID 2045742 반응식
[C:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13](Br)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=O)[CH3:2].[CH:18]1[C:30]2[NH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2C=C[CH:19]=1>[Cu]=O>[CH:15]1[C:16]2[N:4]([C:1]3[CH:19]=[CH:18][C:30]4[NH:29][C:28]5[C:23]([C:22]=4[CH:2]=3)=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 6854CarbazoleHCID 17148799-Acetyl-3-bromocarbazole

생성물 1

HCID 132360229H-3,9'-Bicarbazole수율 82.4%

시약·촉매·용매 1

HCID 14829Copper oxide촉매

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온도
170 °C

실험 절차

A mixture of 4.0 g of 9-Acetyl-3-bromocarbazole prepared as described above and 2.8 g of carbazole were stirred together in 30 ml N,N′-dimethylacetamide. To this was added 0.8 g of copper oxide and heated to 170° C. for 24 h. The reaction was quenched with water and the solid was filtered, washed with methanol, and dried under vacuum. The solid (5.0 g) was then taken up for further deprotection using 1.2 g KOH with THF (6 ml), methanol (12 ml) and water (12 ml) at reflux temperature. The reaction mixture was then extracted using ethylacetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using toluene:hexane (1:2) as eluent, yielded 3.8 g of 3-(9-carbazolyl)carbazole as a white powder.

후처리

  1. customprepared
  2. customThe reaction was quenched with water
  3. filtrationthe solid was filtered
  4. washwashed with methanol
  5. customdried under vacuum
  6. temperatureat reflux temperature
  7. extractionThe reaction mixture was then extracted
  8. dry with materialand the organic layer was dried over anhydrous sodium sulfate
  9. customevaporated to dryness under vacuum

출처 및 근거

ORD 기록
ord-43ed756ca0c243138eb7089c045943fd
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592055B2

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