4-Bromo-2,5-difluoronitrobenzene → 5-Bromo-4-fluoro-2-nitrophenol

HRID 2109750Notes

Reaction equation

HRID 2109750 reaction equation
C[Si](C)(C)[O-:3].[Na+].[Br:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10](F)[CH:9]=1>C1COCC1>[Br:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10]([OH:3])[CH:9]=1

Participants

4

Reactant 2

HCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 23672319Sodium trimethylsilanolate

Product 1

HCID 576341145-Bromo-4-fluoro-2-nitrophenolYield 205.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. customA bright red suspension was formed
  2. temperaturethe mixture was refluxed for 27 hours
  3. concentrationconcentrated
  4. additionWater (6 mL) was added
  5. extractionextracted with DCM (70 mL×2)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-852bc3e0117642e189bf134ac55ba1c4
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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