Nitric Acid → Ethyl 3,5-difluoro-2-nitrobenzoate

HRID 1910262Notes

Reaction equation

HRID 1910262 reaction equation
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[CH2:10]([O:12][C:13](=[O:22])[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=1)[CH3:11]>>[CH2:10]([O:12][C:13](=[O:22])[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[C:15]=1[N+:1]([O-:4])=[O:2])[CH3:11]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2758826Benzoic acid, 3,5-difluoro-, ethyl ester

Product 1

HCID 46311351Ethyl 3,5-difluoro-2-nitrobenzoateYield 80%

Procedure

10.0 mL of conc. HNO3 at 0° C. was slowly treated with 20.0 mL of conc. H2SO4, then 7.6 g (40 mmol) of 3,5-difluoro-benzoic acid ethyl ester. The reaction mixture was warmed up to room temperature and stirred overnight. This mixture was poured into a beaker containing ice. The resulting mixture was extracted with ethyl acetate, washed with cold water and evaporated to produce 7.4 g (32 mmol, 80%) of 3,5-difluoro-2-nitro-benzoic acid ethyl ester. LCMS: 232 (M+1)+.

Workup

  1. additionThis mixture was poured into a beaker
  2. additioncontaining ice
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washwashed with cold water
  5. customevaporated

Sources & evidence

ORD record
ord-cef4801373e246cc9146883a0a7a7b9d
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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