Acetonitrile → 4-(Furan-3-Yl)Benzaldehyde

HRID 1620823

Reaction equation

HRID 1620823 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].C(#N)C.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(OCC)(=O)C>[O:4]1[CH:5]=[CH:6][C:2]([C:12]2[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=2)=[CH:3]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 891643-BromofuranHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 215260454-(Furan-3-Yl)BenzaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial, 3-bromo-furan(590 mg, 4.02 mmol), 4-formyl phenylboronic acid (600 mg, 4.02 mmol) and 7 ml of actonitrile were mixed. 8 ml of 1N aqueous sodium carbonate was then added to the mixture, followed by 5 mole percent of dichlorobis-(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 150° C. for 7 minutes with microwave irradiation. After cooling, 50 ml of ethyl acetate was added, the organic layer was separated, washed with water, dried over sodium sulfate. The organic solvent was evaporated to give crude product, which was purified by ISCO to give 410 mg of 4-furan-3-yl-benzaldehyde, yield: 60%.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe organic solvent was evaporated
  7. customto give crude product, which
  8. customwas purified by ISCO

Sources & evidence

ORD record
ord-31c3c3a4a57c4fcfb670c40f5df1c9fb
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Linked notes

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