Nitric Acid → 2,4-Difluoro-5-nitrobenzoic acid

HRID 1898293Notes

Reaction equation

HRID 1898293 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 741022,4-Difluorobenzoic acid

Product 1

HCID 27828222,4-Difluoro-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

To a cold mixture of 2,4-difluoro benzoic acid (3.0 g, 18.98 mmol) and conc. H2SO4 (10 mL), fuming HNO3 (3 mL) was added at 0° C. The reaction mixture was stirred at 0-5° C. for 14 h and quenched in ice cold water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 3.0 g of the desired product. 1HNMR (DMSO-d6): δ 7.83-7.90 (m, 1H), 8.57-8.62 (m, 1H).

Workup

  1. additionwas added at 0° C
  2. customquenched in ice cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fbc372e08a7c48d6bb05eb8e327678ae
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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