Reacción #748258

Ecuación de reacción

sodium trimethylsilanolate

4-bromo-2,5-difluoronitrobenzene

→

5-bromo-4-fluoro-2-nitrophenol

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA bright red suspension was formed
2. 2
   Temperaturathe mixture was refluxed for 27 hours
3. 3
   Concentraciónconcentrated
4. 4
   workup.ADDITIONWater (6 mL) was added
5. 5
   Extracciónextracted with DCM (70 mL×2)
6. 6
   Concentraciónconcentrated

Procedimiento

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).

Fuente