Sulfuric Acid → 2-Bromo-4-nitrobenzoic acid

HRID 1363419Notes

Reaction equation

HRID 1363419 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 g, 2.34 mmol) was hydrolysed using H2SO4 (2.2 mL) in water (2.7 mL) at 80° C. for 8 h. After completion of reaction, the solution was poured over crushed ice, basified with sodium carbonate and extracted with EtOAc. Aqueous layer was separated, acidified with 1:1 HCl and extracted with EtOAc (3×100 mL). The combined organic layers were concentrated to obtained compound.

Workup

  1. customat 80° C.
  2. customfor 8 h
  3. customAfter completion of reaction
  4. additionthe solution was poured
  5. customover crushed ice
  6. extractionextracted with EtOAc
  7. customAqueous layer was separated
  8. extractionextracted with EtOAc (3×100 mL)
  9. concentrationThe combined organic layers were concentrated
  10. customto obtained compound

Sources & evidence

ORD record
ord-ceb8886b2f554dc8b837fd191929d813
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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