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

HRID 713589Notes

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

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 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 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
Patent number
US09184399B2

Reaction notes

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