Potassium Carbonate → 9-(3'-Bromo-5'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

HRID 713591노트

반응식

HRID 713591 반응식
[Br:1][C:2]1[CH:3]=[C:4]([Si:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6](Br)[CH:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[C:38]([N:42]3[C:54]4[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=4[C:48]4[C:43]3=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:39]=[CH:40][CH:41]=2)O1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.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>[Br:1][C:2]1[CH:7]=[C:6]([C:40]2[CH:41]=[CH:36][CH:37]=[C:38]([N:42]3[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][C:48]=4[C:49]4[C:54]3=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH:39]=2)[CH:5]=[C:4]([Si:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:3]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 586908999-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazoleHCID 58926930HCID 58926930, 화합물

생성물 1

HCID 867009529-(3'-Bromo-5'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)-9H-carbazole수율 79%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A solution of (3,5-dibromophenyl)triphenylsilane (4.02 g, 8.12 mmol), 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (1.500 g, 4.06 mmol), Pd(PPh3)4 (100 mg, 0.086 mmol), K2CO3 (1.123 g, 8.12 mmol) in toluene (100 mL) and water (20 mL) was refluxed under nitrogen for 24 h. After cooling to room temperature, the organic phase was isolated and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane/DCM (9/1 to 4/1, v/v) as eluent and recrystallized from hexane/DCM (9/1, v/v) to yield 9-(3′-Bromo-5′-(triphenylsilyl)-[1,1′-biphenyl]-3-yl)-9H-carbazole (2.1 g, 79%) as white crystals.

후처리

  1. customthe organic phase was isolated
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography on silica gel with hexane/DCM (9/1 to 4/1
  4. customv/v) as eluent and recrystallized from hexane/DCM (9/1

출처 및 근거

ORD 기록
ord-0434bdea024c477a82d5ad9c5ebcfc8d
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09184399B2

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