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

HRID 558185Notes

Reaction equation

HRID 558185 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[F:10][C:11]1[C:19]([F:20])=[C:18]([F:21])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>>[F:10][C:11]1[C:19]([F:20])=[C:18]([F:21])[C:17]([N+:1]([O-:4])=[O:2])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 3029322,3,4-Trifluorobenzoic acid

Product 1

HCID 158712412,3,4-Trifluoro-5-nitrobenzoic acid

Conditions

Temperature
7.5 °C

Procedure

Fuming nitric acid (1.7 ml) is added dropwise to concentrated sulfuric acid (25 ml) while maintaining the temperature at 5-10° C. 2,3,4-Trifluorobenzoic acid (5 g, 28 mmoles) is added in small portion to this solution while keeping the reaction temperature at 5° C. After completion the reaction mixture is stirred at room temperature for an additional 2 hours and poured into ice. The mixture is extracted with ether (3×75 ml). The organic layers are combined, washed with brine, dried (MgSO4). The solvent is removed, and the crude product is recrystallized from hot chloroform to obtain the title compound.

Workup

  1. customat 5° C
  2. additionpoured into ice
  3. extractionThe mixture is extracted with ether (3×75 ml)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed
  7. customthe crude product is recrystallized from hot chloroform

Sources & evidence

ORD record
ord-bfc304592b274883a162ef37e7ae93cb
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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