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Ethanol → 2,7-bis(5-methoxybiphenyl-2-yl)-9-phenyl-9H-carbazole

HRID 1753705
ノート
印刷プレビュー

反応式

HRID 1753705 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]1([N:22]2[C:34]3[CH:33]=[C:32](B4OC(C)(C)C(C)(C)O4)[CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:27]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:53]([O-:56])([O-])=O.[Na+].[Na+].[CH3:59][CH2:60]O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:32]2[CH:31]=[CH:30][C:29]3[C:28]4[C:23](=[CH:24][C:25]([C:2]5[CH:7]=[CH:6][C:5]([O:56][CH3:53])=[CH:4][C:3]=5[C:59]5[CH:60]=[CH:12][CH:11]=[CH:10][CH:15]=5)=[CH:26][CH:27]=4)[N:22]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:34]=3[CH:33]=2)=[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=1
参加物反応条件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 702EthanolHCID 10340Sodium CarbonateHCID 675132132-Bromo-5-methoxy-1,1'-biphenylHCID 902975249-Phenyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

生成物 1

HCID 903427912,7-bis(5-methoxybiphenyl-2-yl)-9-phenyl-9H-carbazole収率 67%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A mixture of 10 g (38.2 mmol) of 2-bromo-5-methoxybiphenyl, 8.6 g (17.4 mmol) of 9-phenyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, 0.4 g (0.35 mmol) of tetrakis(triphenylphosphine)palladium, 30 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 110° C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum. The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (7.1 g, 11.7 mmol, 67%).

後処理

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuum
  7. customThe residue was purified by column chromatography on silica(hexane-dichloromethane)

出典と根拠

ORDレコード
ord-da192fb348db453ba07d52f4efd603be
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09166177B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート