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

HRID 1766216Notes

Reaction equation

HRID 1766216 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-nitrobenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Fuming nitric acid (24 mL) was dissolved in concentrated H2SO4 in a round bottom flask. 3,4-Difluorobromobenzene (20 g, 104 mmol) was added dropwise via pipette with vigorous stirring. After addition was complete, the reaction was allowed to stir at room temperature for 2 hours. The reaction was poured into ice water and extracted 2×250 mL with Et2O. The organic layers were collected, combined, dried over MgSO4, filtered, and the solvent removed leaving a light yellow oil (24.02 g, 97% yield) of 1-bromo-4,5-difluoro-2-nitro-benzene.

Workup

  1. additionAfter addition
  2. extractionextracted 2×250 mL with Et2O
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-a5a9b3c1a5944e6f9600034876ed12af
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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