Nitric Acid → 6-Fluoro-3-nitro-2-(trifluoromethyl)benzeneacetic acid

HRID 2293608Notes

Reaction equation

HRID 2293608 reaction equation
[N+:1]([O-:4])(O)=[O:2].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[C:36]=1[CH2:45][C:46]([OH:48])=[O:47].C(=O)(O)[O-].[Na+]>[N+](CC)([O-])=O>[F:34][C:35]1[C:36]([CH2:45][C:46]([OH:48])=[O:47])=[C:37]([C:41]([F:42])([F:43])[F:44])[C:38]([N+:1]([O-:4])=[O:2])=[CH:39][CH:40]=1

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 27375902-Fluoro-6-(trifluoromethyl)phenylacetic acid

Product 1

HCID 158195216-Fluoro-3-nitro-2-(trifluoromethyl)benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6.33 g (100.62 mmol) of fuming nitric acid (100%) and 25.80 g (91.44 mmol) of trifluoromethanesulfonic anhydride are mixed under ice bath cooling. 200 ml of nitroethane and 12.93 g (91.44 mmol) of phosphorus pentoxide are added to this mixture. 20.31 g (91.44 mmol) of 2-fluoro-6-trifluoromethylphenylacetic acid, suspended in 40 ml of nitroethane, is now instilled under cooling. It is stirred for 1 hour at 0° C. and then allowed to reach room temperature and stirred overnight at room temperature. The thin-layer chromatogram no longer shows starting material. The suspension is poured on 350 ml of cooled, saturated sodium bicarbonate solution. It is extracted three times with dichloromethane. Then, it is acidified with 4N hydrochloric acid, extracted five times with ethyl acetate. The organic phase is washed with water, dried on sodium sulfate and evaporated to dryness in a vacuum. The residue is crystallized from ether/pentane.

Workup

  1. temperaturecooling
  2. temperatureunder cooling
  3. customto reach room temperature
  4. stirringstirred overnight at room temperature
  5. additionThe suspension is poured on 350 ml
  6. temperatureof cooled
  7. extractionIt is extracted three times with dichloromethane
  8. extractionextracted five times with ethyl acetate
  9. washThe organic phase is washed with water
  10. customdried on sodium sulfate
  11. customevaporated to dryness in a vacuum
  12. customThe residue is crystallized from ether/pentane

Sources & evidence

ORD record
ord-5fd3c3a4f21c463195d08bab3f64282c
Source dataset
uspto-grants-1997_11
Patent number
US05686492

Reaction notes

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