Carbazole → 9-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazole

HRID 403151ノート

反応式

HRID 403151 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:16]=[C:17]([Si:21]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Br:40])[CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:19][CH:20]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Br:40][C:36]1[CH:35]=[C:34]([Si:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:17]2[CH:16]=[CH:15][CH:20]=[CH:19][CH:18]=2)[C:22]2[CH:23]=[C:24]([N:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[CH:25]=[CH:26][CH:27]=2)[CH:39]=[CH:38][CH:37]=1

参加物

7

反応物 3

HCID 6854CarbazoleHCID 297508Bis(3-bromophenyl)diphenylsilaneHCID 23676156Sodium t-butoxide

生成物 1

HCID 866740529-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazole収率 49%

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 7237O-Xylene溶媒

実験手順

A suspension of 9H-carbazole (3.60 g, 21.53 mmol), bis(3-bromophenyl)diphenylsilane (21.28 g, 43.1 mmol), Pd2(dba)3 (0.394 g, 0.431 mmol), 1,1′-Bis(diphenylphosphino)ferrocene (dppf, 0.394 g, 0.431 mmol) and sodium tert-butoxide (4.14 g, 43.1 mmol) in xylene (150 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic solution was isolated by filtration. Upon evaporation of the solvent, the crude product was purified by column chromatography on silica gel with hexane:EtOAc (9:1, v/v) as eluent to yield 9-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazole (6.1 g, 49%) as white solid

後処理

  1. temperaturewas refluxed under nitrogen overnight
  2. customthe organic solution was isolated by filtration
  3. customUpon evaporation of the solvent
  4. customthe crude product was purified by column chromatography on silica gel with hexane:EtOAc (9:1

出典と根拠

ORDレコード
ord-17f25f041a3a45359fb9f21bee359959
出典データセット
uspto-grants-2014_06
特許番号
US08748012B2

反応ノート

読み込み中…