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Potassium Carbonate → (3-Bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)triphenylsilane

HRID 713589
Notes
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Reaction equation

HRID 713589 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.[CH:28]1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[C:31](B(O)O)=[CH:30][CH:29]=1.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:3]=[C:4]([Si:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:5]=[C:6]([C:40]2[C:34]3[O:33][C:32]4[CH:31]=[CH:30][CH:29]=[CH:28][C:36]=4[C:35]=3[CH:37]=[CH:38][CH:39]=2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 58926930HCID 58926930, compound

Product 1

HCID 86700950(3-Bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)triphenylsilaneYield 64%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

A solution of (3,5-dibromophenyl)triphenylsilane (4.66 g, 9.43 mmol), dibenzo[b,d]furan-4-ylboronic acid (1.00 g, 4.72 mmol), Pd(PPh3)4 (0.109 g, 0.094 mmol) and potassium carbonate (1.304 g, 9.43 mmol) in toluene (150 mL) and water (25 mL) was refluxed under nitrogen overnight. The organic phase was isolated, filtered and evaporated. The residue was purified by column chromatography on silica gel with hexane/DCM (4/1, v/v) as eluent to yield (3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)triphenylsilane (1.75 g, 64% yield) as a white solid.

Workup

  1. customThe organic phase was isolated
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel with hexane/DCM (4/1

Sources & evidence

ORD record
ord-e1e330a579934a6f849c7f8ca86c5f36
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09184399B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes