Potassium Carbonate → HCID 131727686, compound

HRID 1822083Notes

Reaction equation

HRID 1822083 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](Br)=[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>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.C1(C)C=CC=CC=1>[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 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 131727687HCID 131727687, compound

Product 1

HCID 131727686HCID 131727686, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of the 4-(diallylethoxysilyl)bromobenzene (152 mg, 0.49 mmol) obtained in Example 1, Pd(PPh3)4 (16.9 mg, 0.015 mmol), K2CO3 (101 mg, 0.73 mmol), and phenyl boronic acid (71.4 mg, 0.59 mmol) was added with 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, a salt formed in the reaction mixture 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 was obtained (91.2 mg, 61% yield).

Workup

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

Sources & evidence

ORD record
ord-64c1d0b13b2f42ab9f633749cbd25d66
Source dataset
uspto-grants-2009_10
Patent number
US07608673B2

Reaction notes

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