Potassium Carbonate → Bis-biphenyl-4-yl-amine

HRID 600152

Reaktionsgleichung

Reaktionsgleichung von HRID 600152
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[C:2]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 629950Bis(4-bromophenyl)amine

Produkt 1

HCID 504244Bis-biphenyl-4-yl-amineAusbeute 143,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

In a nitrogen atmosphere, an ethylene glycol dimethyl ether (20 mL) solution containing 9.5 g (29 mmol) of N,N-bis(4-bromophenyl)amine, 7.9 g (65 mmol) of phenyl boronic acid, 0.15 g (0.646 mmol) of palladium acetate, and 1.4 g (4.5 mmol) of tris(o-thryl)phosphine, to which 95 mL of a potassium carbonate solution (2.0 mol/L) is added, is rectified at 90° C. for seven hours. After completion of reaction, the reaction mixture is filtrated, and the obtained solid is recrystallized with chloroform and hexane to obtain 6.7 g (yield: 72%) of N,N-di(4-biphenylyl)amine which is an object as a white powdered solid.

Aufarbeitung

  1. customAfter completion of reaction
  2. filtrationthe reaction mixture is filtrated
  3. customthe obtained solid is recrystallized with chloroform and hexane

Quellen und Nachweise

ORD-Eintrag
ord-3561c060867244a6bf7f7e732bf00c74
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07901792B2

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