Nitric Acid → 4-Bromo-2-fluoro-5-nitroaniline

HRID 622296Notes

Reaction equation

HRID 622296 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:8]([N+:10]([O-:12])=[O:11])=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 138851844-Bromo-2-fluoro-5-nitroanilineYield 22.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 4-bromo-2-fluoroaniline (58.6 g) in conc. sulfuric acid (100 ml), there was dropwise added a mixture of conc. nitric acid (25.3 g) and conc. sulfuric acid (15 ml) at a temperature of 0° to -10° C. The resultant mixture was stirred at 0°-5° C. for 1 hour, poured into ice-water and extracted with toluene. The toluene layer was washed with water and an aqueous sodium hydrogen carbonate solution and concentrated. The residue was purified by silica gel chromatography to give 16.4 g of 4-bromo-2-fluoro-5-nitroaniline. M.P., 90°-92° C.

Workup

  1. extractionextracted with toluene
  2. washThe toluene layer was washed with water
  3. concentrationan aqueous sodium hydrogen carbonate solution and concentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ca65107be398491c8839a1b0b3282c8a
Source dataset
uspto-grants-1988_09
Patent number
US04770695

Reaction notes

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