Реакция #748258

Уравнение реакции

sodium trimethylsilanolate

4-bromo-2,5-difluoronitrobenzene

→

5-bromo-4-fluoro-2-nitrophenol

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеA bright red suspension was formed
2. 2
   Температураthe mixture was refluxed for 27 hours
3. 3
   Концентрированиеconcentrated
4. 4
   workup.ADDITIONWater (6 mL) was added
5. 5
   Экстракцияextracted with DCM (70 mL×2)
6. 6
   Концентрированиеconcentrated

Методика

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).

Источник