Sodium Carbonate → (1,1'-Biphenyl)-4-carboxaldehyde

HRID 965273Notes

Reaction equation

HRID 965273 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=O.[C:12](=[O:15])([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH:12]([C:6]1[CH:7]=[CH:8][C:3]([C:1]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)=[CH:4][CH:5]=1)=[O:15]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

The bromoresin 1-Scheme 10 (1 g, 1 mmol) was swelled in toluene (10 mL) and ethanol (4 mL). To this was added 4-formylphenylboronic acid (450 mg, 3 mmol), aqueous sodium carbonate (2M, 3 mL, 6 mmol) and tetrakistriphenylphosphine palladium (200 mg). The reaction mixture was heated under Argon ("Ar") with stirring for 24 h., cooled and filtered through a sintered glass funnel. Washed the resin with methylene chloride, methanol, methanol-water (1:1), methanol, methylene chloride and finally with methanol. Dried in vacuo to give colorless 4-formylbiphenyl resin 2-Scheme 10. IR (KBr) 1701 cm-1 (CHO).

Workup

  1. temperatureThe reaction mixture was heated under Argon ("Ar")
  2. temperaturecooled
  3. filtrationfiltered through a sintered glass funnel
  4. washWashed the resin with methylene chloride, methanol, methanol-water (1:1), methanol, methylene chloride
  5. customDried in vacuo

Sources & evidence

ORD record
ord-381cb6e853774b66b73ae57a4e0b7ad8
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

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