Reaktion #748258

Reaktionsgleichung

sodium trimethylsilanolate

4-bromo-2,5-difluoronitrobenzene

→

5-bromo-4-fluoro-2-nitrophenol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA bright red suspension was formed
2. 2
   Temperaturthe mixture was refluxed for 27 hours
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONWater (6 mL) was added
5. 5
   Extraktionextracted with DCM (70 mL×2)
6. 6
   Einengenconcentrated

Vorschrift

A solution of 2 M sodium trimethylsilanolate (15.6, 31.1 mmol) in THF was added dropwise to 4-bromo-2,5-difluoronitrobenzene (2.47 g, 10.4 mmol) under a nitrogen atmosphere. A bright red suspension was formed, and the mixture was refluxed for 27 hours. The mixture was cooled to room temperature and concentrated. Water (6 mL) was added, and the solution was acidified with a 10% HCl solution, extracted with DCM (70 mL×2). The organic layers were combined and concentrated to give 5-bromo-4-fluoro-2-nitrophenol (5.05 g, 2.06%). MS m/z: 236 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 7.48 (d, J=5.87 Hz, 1H), 7.95 (d, J=8.41 Hz, 1H).

Quelle