Carbazole → 9H-3,9'-Bicarbazole

HRID 2045742ノート

反応式

HRID 2045742 の反応式
[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

参加物

4

反応物 2

HCID 6854CarbazoleHCID 17148799-Acetyl-3-bromocarbazole

生成物 1

HCID 132360229H-3,9'-Bicarbazole収率 82.4%

試薬・触媒・溶媒 1

HCID 14829Copper oxide触媒

反応条件

温度
170 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-43ed756ca0c243138eb7089c045943fd
出典データセット
uspto-grants-2013_11
特許番号
US08592055B2

反応ノート

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