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

HRID 403151노트

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HRID 403151 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 7237O-Xylene용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-17f25f041a3a45359fb9f21bee359959
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748012B2

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