Sodium Carbonate → 5-(3-Nitrophenyl)furfural

HRID 409937

Reaction equation

HRID 409937 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH:11]([C:13]1[O:17][C:16](B(O)O)=[CH:15][CH:14]=1)=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[N+:8]([C:4]1[CH:3]=[C:2]([C:16]2[O:17][C:13]([CH:11]=[O:12])=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11457Benzene, 1-bromo-3-nitro-HCID 27343555-Formylfuran-2-boronic acid

Product 1

HCID 6124175-(3-Nitrophenyl)furfural

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1.5 g of 1-bromo-3-nitrobenzene (7.42 mmol), 1 g of 5-formyl-2-furanboronic acid (7.42 mmol), and 35 mL of a solution of saturated sodium carbonate (Na2CO3) in 0.2 M tetrahydrofuran was added 0.2 g of tetrakis triphenylphosphine palladium [Pd(PPh3)4] (0.2 mmol) at room temperature with stirring. After completion of the addition, the resulting mixture was heated for an additional 12 hrs, cooled to room temperature, and concentrated in vacuo. The concentrate was extracted with methylene chloride, and the organic layer thus formed was added, washed with saturated brine, dried over magnesium sulfate, and concentrated in a vacuum. Purification by silica gel column chromatography afforded the title compound.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe resulting mixture was heated for an additional 12 hrs
  3. concentrationconcentrated in vacuo
  4. extractionThe concentrate was extracted with methylene chloride
  5. customthe organic layer thus formed
  6. additionwas added
  7. washwashed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in a vacuum
  10. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-ae80ef80a6d947c0bbcbba4fb440f97b
Source dataset
uspto-grants-2014_06
Patent number
US08759536B2

Linked notes

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