Ammonium Chloride → 3-Bromo-5-(difluoromethyl)aniline

HRID 1040031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040031
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH:11]([F:13])[F:12])[CH:3]=1.[NH4+].[Cl-]>C(O)C.O.C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH:11]([F:12])[F:13])[CH:3]=1)[NH2:8]

Komponenten

7

Edukt 2

HCID 25517Ammonium ChlorideHCID 672481711-Bromo-3-(difluoromethyl)-5-nitrobenzene

Produkt 1

HCID 584563863-Bromo-5-(difluoromethyl)anilineAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Iron (1.99 g, 35.7 mmol) was added to a vigorously stirred mixture of 1-bromo-3-(difluoromethyl)-5-nitrobenzene (1.80 g, 7.14 mmol) and NH4Cl (0.191 g, 3.57 mmol) in ethanol (30 mL) and water (15 mL). The mixture was heated to 95° C. for 2 h. It was then diluted with ethyl acetate while still hot and filtered over Celite. The filtrate was washed with dilute aqueous NaHCO3 and brine. After solvent evaporation the residue was purified through a silica plug, eluting with 1:5 ethyl acetate:hexanes to yield 3-bromo-5-(difluoromethyl)aniline (1.3 g, 5.86 mmol, 82%).

Aufarbeitung

  1. filtrationfiltered over Celite
  2. washThe filtrate was washed with dilute aqueous NaHCO3 and brine
  3. customAfter solvent evaporation the residue
  4. customwas purified through a silica plug
  5. washeluting with 1:5 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-42645d21227d45138c896c2aef8ff410
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551984B2

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