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

HRID 1852342Notes

Reaction equation

HRID 1852342 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 5 g portions over 90 minutes. The dark brownish yellow solution is stirred for 60 min 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 min 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 min at which time the reaction
  2. extractionwater mixture and extracted 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 min after which time it
  7. filtrationis filtered

Sources & evidence

ORD record
ord-eac1b843de444ef8a4e2924feda4ef86
Source dataset
uspto-grants-2015_02
Patent number
US08961970B2

Reaction notes

Loading…