Sodium Carbonate → 2-(Furan-3-yl)benzaldehyde

HRID 1620868Notes

Reaction equation

HRID 1620868 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O)=[O:2].Br[C:13]1[CH:17]=[CH:16][O:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[O:15]1[CH:16]=[CH:17][C:13]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[O:2])=[CH:14]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 891643-BromofuranHCID 2921892-Formylphenylboronic acid

Product 1

HCID 183576172-(Furan-3-yl)benzaldehydeYield 31.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial (20 ml) was charged with 2-formylphenylboronic acid (298 mg, 2.0 mmol), 3-bromo-furan (350 mg, 2.4 mmol) and 8 ml of acetonitrile. To this mixture was added 4 ml of aqueous sodium carbonate (1M), followed by 100 mg of dichlorobis-(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 150° C. for 5 minutes with microwave irradiation. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was evaporated to provide crude material which was purified by ISCO to give 110 mg of 2-furan-3-yl-benzaldehyde (30% yield).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. customThe organic layer was evaporated
  5. customto provide crude material which
  6. customwas purified by ISCO

Sources & evidence

ORD record
ord-6d01c13de9b345f09b378662a0d2d922
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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