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Benzene → 3-(Biphenyl-4-yl)furan

HRID 382127
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 382127
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].[C:19]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>CCO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:19]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:24]=[CH:23][C:22]([C:2]2[CH:6]=[CH:5][O:4][CH:3]=2)=[CH:21][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 891643-BromofuranHCID 1512531,1'-Biphenyl-4-yl-boronic acid

Produkt 1

HCID 183802933-(Biphenyl-4-yl)furanAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A biphasic mixture of 3-bromofuran (2.90 mL, 32.1 mmol), benzene (70 mL), and 2N aqueous Na2CO3 (50 mL) was degassed and purged with argon. Tetrakis(triphenylphosphine) palladium(0) (3.7 g, 3.2 mmol) arid a solution of 4-biphenylboronic acid (6.3 g, 32.1 mmol) in EtOH (50 mL) were added sequentially. The mixture was heated at 80° C. for 18 hours, allowed to cool, and partitioned between CH2Cl2 and H2O. The aqueous layer was separated and extracted with CH2Cl2 two times. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to a crude product, which was dissolved in a minimal amount of CH2Cl2 and applied to a flash chromatography column packed with hexanes. Elution with 10% CH2Cl2/hex led to some mixed fractions, which were rechromatographed. A total of 5.37 g (76%) of 3-(biphenyl-4-yl)furan was obtained as a pale yellow oil.

Aufarbeitung

  1. customwas degassed
  2. custompurged with argon
  3. additionwere added sequentially
  4. temperatureto cool
  5. custompartitioned between CH2Cl2 and H2O
  6. customThe aqueous layer was separated
  7. extractionextracted with CH2Cl2 two times
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated to a crude product, which
  11. dissolutionwas dissolved in a minimal amount of CH2Cl2
  12. washElution with 10% CH2Cl2/hex
  13. customwere rechromatographed

Quellen und Nachweise

ORD-Eintrag
ord-da12ee5354e847e8beb2d47e19e329f0
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06306892B1

Notizen zur Reaktion

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