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

HRID 887661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887661
[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 27757093-Nitro-5-(trifluoromethyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e474329f04a44bdbb4a3f882c2beb713
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247430B2

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