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

HRID 713591Notes

Reaction equation

HRID 713591 reaction equation
[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

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 58690899(3-(carbazole-9H)Phenyl)Pinacol esterHCID 58926930HCID 58926930, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0434bdea024c477a82d5ad9c5ebcfc8d
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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