Sulfuric Acid → 2-Bromo-4-nitrobenzoic acid

HRID 916719Notes

Reaction equation

HRID 916719 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1C#N.OS(O)(=O)=O.[C:18](=[O:21])([O-])[O-:19].[Na+].[Na+]>O>[Br:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:18]([OH:19])=[O:21]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 223512982-Bromo-4-nitrobenzonitrile

Product 1

HCID 3135342-Bromo-4-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromo-4-nitro-benzonitrile (0.5 gm, 2.34 mmol) was hydrolysed using H2SO4 (2.2 ml) in 2.7 ml water at 80° C. for 8 hrs. After completion of reaction solution was poured over crushed ice, basified with sodium carbonate and extracted with ethyl acetate. Aqueous layer was separated, acidified with 1:1 HCl and extracted with ethyl acetate. Combined organic layer was then concentrated to obtained compound(51).

Workup

  1. customat 80° C.
  2. customfor 8 hrs
  3. customAfter completion of reaction solution
  4. additionwas poured
  5. customover crushed ice
  6. extractionextracted with ethyl acetate
  7. customAqueous layer was separated
  8. extractionextracted with ethyl acetate
  9. concentrationCombined organic layer was then concentrated
  10. customto obtained compound(51)

Sources & evidence

ORD record
ord-3a1f71df2dfe4765b74e5b9db35fb154
Source dataset
uspto-grants-2007_09
Patent number
US07271193B2

Reaction notes

Loading…