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Carbazole → HCID 57879967、化合物

HRID 1816865
ノート
印刷プレビュー

反応式

HRID 1816865 の反応式
N[CH:2]([NH2:4])[CH3:3].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:14]1[CH:19]=[C:18]([Br:20])[C:17](Br)=[CH:16][C:15]=1[Br:22].[CH:23]1[C:35]2[NH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1>[Cu](I)I.O1CCOCC1>[Br:22][C:15]1[C:14]([N:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:35]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:19][C:18]([Br:20])=[C:17]([N:4]2[C:2]3[CH:3]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:26]2=[CH:25][CH:24]=[CH:23][CH:35]=3)[CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6854CarbazoleHCID 124861,2,4,5-TetrabromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 5242187Ethane-1,1-diamine

生成物 1

HCID 57879967HCID 57879967、化合物収率 5.2%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

1.16 g (6.1 mmole) of copper iodide and 200 ml of anhydrous dioxane were put in a three-necked flask of 300 ml, 0.41 ml (6.1 mmole) of diaminoethane was dropped at room temperature under nitrogen flow, and the mixture was stirred for 15 minutes at room temperature and heated to 60° C. This solution was allowed to cool to room temperature, 56.8 g (244 mmole) of potassium phosphate, 12.0 g (30.5 mmole) of 1,2,4,5-tetrabromobenzene and 40.8 g (244 mmole) carbazole were added, and heated with stirring at 80° C. under nitrogen flow for 48 hours. After the reaction was completed, the reaction mixture was hot-filtered using Celite to remove insoluble matter. The filtrate was concentrated under reduced pressure. The residue was refined by NH-modified silica gel silica gel column chromatography (eluent:hexane/toluene: 1/2). The obtained crystal was repeatedly recrystallized from toluene and chloroform to give 0.90 g of a white crystal of 1,4-dibromo-3,6-di(carbazole-9-yl)benzene (yield: 5.2%). By reacting two equivalent weight of 4-(2-phenylindole-1-yl)phenyl boronic acid with this 1,4-dibromo-3,6-di(carbazole-9-yl)benzene, 1,4-di(carbazole-9-yl)-2,5-bis{4-(2-phenylindole-1-yl)phenyl}benzene was obtained. The melting point of this compound was 376° C., and the glass transition temperature was 184° C.

後処理

  1. additionwas dropped at room temperature under nitrogen flow
  2. temperatureheated to 60° C
  3. temperatureto cool to room temperature
  4. temperatureheated
  5. stirringwith stirring at 80° C. under nitrogen flow for 48 hours
  6. filtrationthe reaction mixture was hot-filtered
  7. customto remove insoluble matter
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe obtained crystal was repeatedly recrystallized from toluene and chloroform

出典と根拠

ORDレコード
ord-6579419ae27f4418bd34a4bf282f7b07
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07597955B2

反応ノート

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