Reaction #748258

Reaction equation

sodium trimethylsilanolate

4-bromo-2,5-difluoronitrobenzene

→

5-bromo-4-fluoro-2-nitrophenol

Solvents

THF

Conditions

Workup

1. 1
   OtherA bright red suspension was formed
2. 2
   Temperaturethe mixture was refluxed for 27 hours
3. 3
   Concentrationconcentrated
4. 4
   workup.ADDITIONWater (6 mL) was added
5. 5
   Extractionextracted with DCM (70 mL×2)
6. 6
   Concentrationconcentrated

Procedure

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).

Source