Nitric Acid → 1-Bromo-4,5-difluoro-2-nitrobenzene

HRID 1371869Notes

Reaction equation

HRID 1371869 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([Br:13])[CH:9]=[CH:10][C:11]=1[F:12]>OS(O)(=O)=O>[Br:13][C:8]1[CH:7]=[C:6]([F:5])[C:11]([F:12])=[CH:10][C:9]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 676754-Bromo-1,2-difluorobenzene

Product 1

HCID 192615421-Bromo-4,5-difluoro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Dissolve fuming nitric acid (24 mL) in concentrated H2SO4 in a round bottom flask. Add 3,4-difluorobromobenzene (20 g, 104 mmol) dropwise via pipette with vigorous stirring. After addition, stir the reaction at room temperature for 2 hours, pour the reaction into ice water and extract with Et2O (2×250 mL). Collect and combine the organic layers, dry over MgSO4, filter, and remove the solvent to give 1-bromo-4,5-difluoro-2-nitrobenzene as a light yellow oil.

Workup

  1. additionAfter addition
  2. customthe reaction at room temperature for 2 hours
  3. additionpour
  4. extractionextract with Et2O (2×250 mL)
  5. customCollect
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customremove the solvent

Sources & evidence

ORD record
ord-5676f527c8e04ccf8357b5bfa1826314
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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