Aniline → N-phenyl-2-Dibenzofuranamine

HRID 634544

Reaktionsgleichung

Reaktionsgleichung von HRID 634544
Br[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:16]1([NH:15][C:12]2[CH:13]=[CH:14][C:9]3[O:8][C:7]4[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=4[C:10]=3[CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 3

HCID 6115AnilineHCID 4582564-Bromodibenzo[b,d]furanHCID 23676156Sodium t-butoxide

Produkt 1

HCID 67204676N-phenyl-2-DibenzofuranamineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 634876Binap, (A+-)-KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-bromodibenzo[b,d]furan (3.0 g, 12.1 mmol) and aniline (1.69 g, 18.1 mmol) were mixed in 100 mL of toluene. The solution was bubbled with nitrogen for 15 min. Pd2(dba)3 (0.05 g, 0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.15 g, 0.24 mmol) and sodium t-butoxide (1.7 g, 17.4 mmol) were added. The mixture was refluxed overnight under nitrogen. After cooling, the reaction mixture was filtered through celite/silica pad and the filtrate was concentrated under vacuum. The residue was then purified by column chromatography using DCM:hexane (1:1, v/v) as the eluent. 2.0 g (65%) of a white solid was obtained as the product.

Aufarbeitung

  1. customThe solution was bubbled with nitrogen for 15 min
  2. temperatureThe mixture was refluxed overnight under nitrogen
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through celite/silica pad
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residue was then purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d5f29dc01bfa4e10ac9c9be8b6866ec3
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09324949B2

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