Reaktion #726240

ord-58c379775e6d4835be1e2d6d6602a777

Reaktionsgleichung

O=[N+]([O-])c1ncccc1O
3-Hydroxy-2-nitropyridine
C[O-].[Na+]
sodium methoxide
BrBr
bromine
O=[N+]([O-])c1nc(Br)ccc1O
material
Ausbeute 97.9%
O=[N+]([O-])c1nc(Br)ccc1O
2-Bromo-5-hydroxy-6-nitropyridine
Ausbeute 97.9%

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGThe reaction was stirred at 0° C. for 30 min
  2. 2
    Sonstigewas quenched with glacial AcOH (2.5 mL)
  3. 3
    SonstigeThe solvent was removed in vacuo

Vorschrift

3-Hydroxy-2-nitropyridine (20 g, 0.143 mole) was dissolved in methanol (400 mL) and a solution of 25% sodium methoxide in methanol (33 mL, 0.13 mole) was added at room temperature. The mixture was stirred for 30 min, then was cooled to 0° C., and bromine (7.2 mL, 0.14 mole) was added slowly. The reaction was stirred at 0° C. for 30 min, then was quenched with glacial AcOH (2.5 mL). The solvent was removed in vacuo to afford material (30 g, 96%), which was used without further purification.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07691850B2uspto-grants-2010_04