Benzyl Bromide → 2-Benzyloxy-4,5-difluoronitrobenzene

HRID 660831Notes

Reaction equation

HRID 660831 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([F:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27741824,5-Difluoro-2-nitrophenol

Product 1

HCID 688400302-Benzyloxy-4,5-difluoronitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a vigorously stirred mixture of 4,5-difluoro-2-nitrophenol (1 g, 5.71 mmol) and anhydrous potassium carbonate (1.9 g, 14.28 mmol) in acetone (20 mL). is added benzyl bromide (750 μl, 6.28 mmol) and the dark heterogeneous mixture is heated to reflux for 10 h; or until all starting material had been consumed according to LC/MS analysis. The dark mixture is then filtered, dried over magnesium sulfate, and filtered again to afford, after solvent removal, a light brown crystalline solid that was used in the next step without further purification.

Workup

  1. temperaturethe dark heterogeneous mixture is heated
  2. temperatureto reflux for 10 h
  3. customor until all starting material had been consumed
  4. filtrationThe dark mixture is then filtered
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered again
  7. customto afford
  8. customafter solvent removal
  9. customa light brown crystalline solid that was used in the next step without further purification

Sources & evidence

ORD record
ord-e27f13424c964523a059667bbc9feb36
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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