Water → 2-(4-Nitrophenoxy)naphthalene

HRID 17711

Reaktionsgleichung

Reaktionsgleichung von HRID 17711
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+].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[OH:27].O>CN(C=O)C>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[O:27][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 86632-NaphtholHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Produkt 1

HCID 7624782-(4-Nitrophenoxy)naphthalene

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 rt, solid potassium carbonate (30 mmol) was added followed by addition of 2-naphthol (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 rt, the reaction mixture was poured into H2O (100 mL), extracted with EtOAc (2×50 mL), washed with H2O (2×50 mL) and brine (50 mL), and dried over sodium sulfate. The solvent was removed in vacuuo to afford the desired 4-(naphthalen-2-yloxy)-1-nitrobenzene. The crude product was used for further transformation.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×50 mL)
  3. washwashed with H2O (2×50 mL) and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuuo

Quellen und Nachweise

ORD-Eintrag
ord-1664b3d3dece41298e5c5de6da7e1577
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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