Nitric Acid → 4,5-Difluoro-2-nitrophenol

HRID 660830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660830
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[N+:10]([O-])([OH:12])=[O:11].S([O-])([O-])(=O)=O.[Mg+2]>ClCCl.S([O-])([O-])(=O)=O.[Ni+].[NH4+]>[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=1

Komponenten

6

Edukt 3

HCID 944Nitric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 759273,4-Difluorophenol

Produkt 1

HCID 27741824,5-Difluoro-2-nitrophenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 171000000CID 171000000KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3,4-difluorophenol (1.56 g, 7.69 mmol) in dichloromethane (10 mL) under a blanket of nitrogen is added ammonium nickel sulfate (2.0 g, 5.07 mmol), with vigorous stirring, followed by the addition of nitric acid (69%, 0.770 mL, 7.69 mmol). The resulting heterogeneous mixture is then stirred at RT for 5-10 min; at this point a bright orange solution was observed along with a mild exothermic gaseous emission. (LC/MS indicated the formation of one single product.) Anhydrous magnesium sulfate (˜1 g) is then added to the reaction mixture, which is stirred and filtered to afford an orange solution. Removal of dichloromethane under reduced pressure affords an orange solid residue. (low melting solid, sublimed upon storage) 1H NMR (400 MHz, δ, CDCl3): 10.61 (s, 1H), 8.01 (m, 1H), 7.00 (m, 1H).

Aufarbeitung

  1. stirringis stirred
  2. filtrationfiltered
  3. customto afford an orange solution
  4. customRemoval of dichloromethane under reduced pressure
  5. customaffords an orange solid residue

Quellen und Nachweise

ORD-Eintrag
ord-24b30ef56a0044b098d313b005ea4b25
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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