Nitric Acid → 2,4,5-Trifluoro-3-methoxy-6-nitrobenzoic acid

HRID 1367981Notes

Reaction equation

HRID 1367981 reaction equation
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[CH3:10][O:11][C:12]1[C:13]([F:23])=[C:14]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:15]([OH:17])=[O:16]>>[CH3:10][O:11][C:12]1[C:13]([F:23])=[C:14]([C:18]([N+:1]([O-:4])=[O:2])=[C:19]([F:22])[C:20]=1[F:21])[C:15]([OH:17])=[O:16]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 27339702,4,5-Trifluoro-3-methoxybenzoic acid

Product 1

HCID 218054742,4,5-Trifluoro-3-methoxy-6-nitrobenzoic acidYield 80%

Procedure

5.0 mL of conc. HNO3 at 0° C. was slowly treated with 10.0 mL of conc. H2SO4, then 4.12 g (20 mmol) of 3-methoxy-2,4,5-trifluoro-benzoic acid. The reaction mixture was warmed to room temperature and stirred overnight. The mixture was poured in to a beaker containing ice. The resulting solid was collected by filtration, washed with cold water and dried to produce 4.0 g (16 mmol, 80%) of 3-methoxy-6-nitro-2,4,5-trifluoro-benzoic acid. LCMS: 252 (M+1)+.

Workup

  1. additionThe mixture was poured in to a beaker
  2. additioncontaining ice
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with cold water
  5. customdried

Sources & evidence

ORD record
ord-b335df89f36548a6abb7dee57a626df1
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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