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

HRID 1761326Notes

Reaction equation

HRID 1761326 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 is 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 is stirred at 0°-5° C. for 1 hour, poured into ice-water and extracted with toluene. The toluene layer is washed with water and an aqueous sodium hydrogen carbonate solution and concentrated. The residue is 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 is washed with water
  3. concentrationan aqueous sodium hydrogen carbonate solution and concentrated
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-86f946524216475c95e1add44106b2f0
Source dataset
uspto-grants-1989_05
Patent number
US04826533

Reaction notes

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