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

HRID 1009983Notes

Reaction equation

HRID 1009983 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[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+:6]([O-:9])=[O:7])=[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 acidYield 92%

Procedure

A 3 liter three neck round bottom flask is charged with 125 mL H2SO4. Fuming nitric acid is added (8.4 mL, 199 mmol) and the mixture gently stirred. 2,3,4-Trifluorobenzoic acid 1 (25 g, 142 mmol) is added in 5g portions over 90 minutes. The dark brownish yellow solution is stirred for 60 minutes at which time the reaction is complete. The reaction mixture is poured into 1 liter of an ice water mixture and extracted with diethyl ether (3×600 mL). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid is suspended in hexanes and stirred for 30 minutes after which time it is filtered to give 29 g (92%) of clean desired product as an off-yellow solid: MS APCI (−) m/z 220 (M−1) detected.

Workup

  1. stirringThe dark brownish yellow solution is stirred for 60 minutes at which time the reaction
  2. extractionextracted with diethyl ether (3×600 mL)
  3. dry with materialThe combined organic extracts are dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow solid
  6. stirringstirred for 30 minutes after which time it
  7. filtrationis filtered

Sources & evidence

ORD record
ord-0e0706f8f5d6423b8bc046919f4613b5
Source dataset
uspto-grants-2011_07
Patent number
US07973170B2

Reaction notes

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