Sodium Carbonate → 2-(Furan-2-yl)aniline

HRID 558984

Reaktionsgleichung

Reaktionsgleichung von HRID 558984
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 119922-BromoanilineHCID 2734357Furan-2-boronic acid

Produkt 1

HCID 46853502-(Furan-2-yl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-bromoaniline (137 mg, 0.80 mmol) in THF (4.0 ml) was added 2-furanboronic acid (89 mg, 0.80 mmol), tetrakis-(triphenylphosphine)palladium (0) (92 mg, 0.08 mmol) and sodium carbonate solution (2M, 2.0 ml, 4.0 mmol). The mixture was heated in a sealed tube using a microwave reactor (20 W) at 130° C. for 25 min. This procedure was carried out 5 times and the reaction mixtures were combined. The mixture was separated and the aqueous layer extracted with EtOAc. The combined organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil; yield 211 mg, 33%.

Aufarbeitung

  1. temperatureThe mixture was heated in a sealed tube
  2. customat 130° C.
  3. customfor 25 min
  4. customthe reaction mixtures
  5. customThe mixture was separated
  6. extractionthe aqueous layer extracted with EtOAc
  7. customThe combined organic layers were dried
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15)
  10. customto give a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-940efed197184e388209bc0404d88a2d
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063038B2

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