alpha,alpha,alpha-Trifluoro-3,5-dinitrotoluene → 3-Nitro-5-(trifluoromethyl)aniline

HRID 887661Notes

Reaction equation

HRID 887661 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-])=O.[NH4+]=S>CCO.O>[N+:10]([C:8]1[CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]([C:13]([F:14])([F:15])[F:16])[CH:7]=1)([O-:12])=[O:11]

Participants

4

Reactant 1

HCID 123060alpha,alpha,alpha-Trifluoro-3,5-dinitrotoluene

Product 1

HCID 27757093-Nitro-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3,5-dinitrobenzotrifluoride (10 g, 42 mmols, 1 eq.) in 150 mL of EtOH was added 17.6 mL (258.3 mmols, 6.15 eq.) of ammonium sulfide in water (50% by weight, Aldrich). The reaction was heated to reflux for 16 h during which time it became orange and a yellow precipitate formed. After cooling the volume was reduced to approximately 50 mL. The solid was removed by filtration and the filtrate evaporated to dryness in vacuo. The resulting orange solid was purified by column chromatography eluting with a step gradient of 20-30% EtOAc:hexane to provide the compound as a yellow/orange solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 16 h during which time it
  3. customa yellow precipitate formed
  4. temperatureAfter cooling the volume
  5. customThe solid was removed by filtration
  6. customthe filtrate evaporated to dryness in vacuo
  7. customThe resulting orange solid was purified by column chromatography
  8. washeluting with a step gradient of 20-30% EtOAc

Sources & evidence

ORD record
ord-e474329f04a44bdbb4a3f882c2beb713
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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