Reaktion #2075744

ord-f2878d34def94adfafcddeb541d87691

Reaktionsgleichung

CI
MeI
O=[N+]([O-])c1ccccc1O
nitrophenol
O=[N+]([O-])c1cccc(O)c1Cl
C2
O=[N+]([O-])c1cccc(O)c1Cl
2-chloro-3-nitrophenol
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
COc1cccc([N+](=O)[O-])c1Cl
2-chloro-3-nitroanisole
Ausbeute 98.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe DMF was evaporated in vacuo
  2. 2
    Waschenwashed with water (150 mL), brine (4×100 mL)
  3. 3
    Trocknendried over (MgSO4)
  4. 4
    FiltrationThe organic phase was filtered
  5. 5
    Sonstigeevaporated

Vorschrift

The nitrophenol starting material C2 (1.3 g; 7.49 mmol) was dissolved in DMF (10 mL) and to this solution was added ground cesium carbonate (2.92 g; 8.96 mmol), followed by MeI (1.4 mL; 22.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated in vacuo and the residue taken up in ether (150 mL), washed with water (150 mL), brine (4×100 mL), and then dried over (MgSO4). The organic phase was filtered and evaporated to afford the crude 2-chloro-3-nitroanisole C3 (98%; 1.38 g) as an orange solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07642235B2uspto-grants-2010_01