Réaction #2075741

ord-d13b3930d3c9441e944919e292ea729c

Équation de réaction

CI
MeI
O=[N+]([O-])c1ccccc1O
nitrophenol
O=[N+]([O-])c1cccc(O)c1Br
B2
O=[N+]([O-])c1cccc(O)c1Br
2-bromo-3-nitrophenol
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
COc1cccc([N+](=O)[O-])c1Br
2-bromo-3-nitroanisole
Rendement 94.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe DMF was evaporated
  2. 2
    Lavagewashed with water (1×200 mL), brine (4×100 mL)
  3. 3
    Séchagedried (MgSO4)
  4. 4
    Filtrationfiltered
  5. 5
    Autreevaporated

Mode opératoire

The nitrophenol starting material B2 (3.1 g; 14.2 mmol) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1 mmol) followed by MeI (2.6 mL; 42.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1×200 mL), washed with water (1×200 mL), brine (4×100 mL), dried (MgSO4), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole B3 (94%; 3.1 g) as an orange solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07642235B2uspto-grants-2010_01