Nitric Acid → Ethyl 2,4-difluoro-5-nitrobenzoate

HRID 1410214Notes

Reaction equation

HRID 1410214 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].OS(O)(=O)=O>>[F:5][C:6]1[CH:16]=[C:15]([F:17])[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2737170Benzoic acid, 2,4-difluoro-, ethyl ester

Product 1

HCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Procedure

Conc. HNO3 (8 mL) was added dropwise to a mixture of ethyl 2,4-difluorobenzoate (10.0 g; 53.7 mmol) in cone. H2SO4 (8 mL) at 0° C. After 2 h at 0° C., the mixture was poured onto ice and extracted with EtOAc. The organic extracts were washed with saturated NaHCO3 solution (aq) and concentrated to give the sub-title compound. Yield: 11.8 g (95%).

Workup

  1. customat 0° C
  2. additionthe mixture was poured onto ice
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with saturated NaHCO3 solution (aq)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d5cf0b6e3e914cc39202a71b2dd64ac5
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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