Potassium Carbonate → HCID 57894272, compound

HRID 1822086Notes

Reaction equation

HRID 1822086 reaction equation
C(C(CC=C)C[O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)C=C.C([O-])([O-])=O.[K+].[K+].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=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>[CH2:13]([Si:7]([CH2:12][CH:11]=[CH2:10])([OH:6])[C:8]1[CH:9]=[CH:10][C:11]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:12][CH:13]=1)[CH:8]=[CH2:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 131727682HCID 131727682, compound

Product 1

HCID 57894272HCID 57894272, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of the 4-(diallylhydroxysilyl)iodobenzene (151 mg, 0.46 mmol) obtained in Example 17, Pd(PPh3)4 (15.9 mg, 0.014 mmol), K2CO3 (94.8 mg, 0.69 mmol), and 4-methoxyphenyl boronic acid (83.4 mg, 0.55 mmol) was added with dist.toluene (5 mL). Subsequently, the resultant mixture was stirred under a nitrogen atmosphere at 80° C. for 38 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=3/1), and thereby 4-(diallylhydroxysilyl)-4′-methoxybiphenyl was obtained (76.1 mg, 54% 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=3/1)

Sources & evidence

ORD record
ord-6fafdc0ea1a14b20a28dbb375bec0e23
Source dataset
uspto-grants-2009_10
Patent number
US07608673B2

Reaction notes

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