Toluene → HCID 131727686, compound

HRID 1822082Notes

Reaction equation

HRID 1822082 reaction equation
[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC=CC=1>CCOCC>[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 131727682HCID 131727682, compound

Product 1

HCID 131727686HCID 131727686, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At first, a mixture of the 4-(diallylethoxysilyl)iodobenzene (148 mg, 0.41 mmol) obtained in Example 2, tetrakistriphenylphosphine palladium (Pd(PPh3)4: 14.3 mg, 0.012 mmol), potassium carbonate (K2CO3: 85.1 mg, 0.62 mmol), and phenyl boronic acid (60 mg, 0.49 mmol) was added with distilled toluene (dist.toluene: 5 mL). Subsequently, the resultant mixture was stirred under a nitrogen atmosphere at 80° C. for 13 hours to obtain a reaction mixture. Thereafter, the reaction mixture was diluted with ether, and a salt thus formed was removed by filtering with celite. The solvent was distilled from the organic layer with an evaporator to obtain a crude product. After that, the crude product thus obtained was separated and purified by silica gel column chromatography (hexane/EtOAc=10/1), and thereby 4-(diallylethoxysilyl)biphenyl (a second organosilane compound of the present invention) was obtained (99.6 mg, 78% yield).

Workup

  1. customto obtain a reaction mixture
  2. customa salt thus formed
  3. customwas removed
  4. filtrationby filtering with celite
  5. distillationThe solvent was distilled from the organic layer with an evaporator
  6. customto obtain a crude product
  7. customAfter that, the crude product thus obtained
  8. customwas separated
  9. custompurified by silica gel column chromatography (hexane/EtOAc=10/1)

Sources & evidence

ORD record
ord-47dad95ffa3244c8822b598b53afa88f
Source dataset
uspto-grants-2009_10
Patent number
US07608673B2

Reaction notes

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