Sodium Carbonate → 5-(3-Nitrophenyl)furfural

HRID 409937

Reaktionsgleichung

Reaktionsgleichung von HRID 409937
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 6124175-(3-Nitrophenyl)furfural

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ae80ef80a6d947c0bbcbba4fb440f97b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759536B2

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