4-Hydroxybiphenyl → 4-(4-Nitrophenoxy)-1,1'-biphenyl

HRID 17729

Reaktionsgleichung

Reaktionsgleichung von HRID 17729
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.CCOC(C)=O>CN(C=O)C>[C:21]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][C:18]([O:17][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 71034-HydroxybiphenylHCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Produkt 1

HCID 2408644-(4-Nitrophenoxy)-1,1'-biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 1-fluoro-4-nitrobenzene (10 mmol) in DMF (20 mL) at room temperature, solid K2CO3 (30 mmol) was added followed by addition of 4-hydroxybiphenyl (10 mmol) to the reaction mixture and heating to 80° C. until the reaction was complete as indicated by TLC or HPLC. After cooling to room temperature to room temperature, the reaction mixture was poured into EtOAc (100 mL), washed with water (2×50 mL) and brine (50 mL), and dried over sodium sulfate. The solvent was removed in vacuo to afford the desired 4-(biphenyl-4-oxy)-1-nitrobenzene. The crude product was used for further transformation.

Aufarbeitung

  1. temperatureAfter cooling to room temperature to room temperature
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1bf6e80c0a96446baa085c6ab281ef86
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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