Nitric Acid → 3-Fluoro-4-hydroxy-5-nitrobenzonitrile

HRID 1258740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258740
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[C:9]#[N:10]>OS(O)(=O)=O>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([N+:1]([O-:4])=[O:2])[C:13]=1[OH:14])[C:9]#[N:10]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 27829443-Fluoro-4-hydroxybenzonitrile

Produkt 1

HCID 679577893-Fluoro-4-hydroxy-5-nitrobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Fuming HNO3 (1.8 mL; 44 mmol) was added dropwise to a solution of 3-fluoro-4-hydroxybenzonitrile (4.0 g; 29 mmol) in conc. H2SO4 (10 mL) at −10° C. The mixture was stirred at −10° C. for 1 h and thereafter slowly poured into ice. The precipitate was filtered off and the filtrate was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was combined with the precipitate and crystallized from EtOAc/PE to give the sub-title compound.

Aufarbeitung

  1. additionslowly poured into ice
  2. filtrationThe precipitate was filtered off
  3. extractionthe filtrate was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customcrystallized from EtOAc/PE

Quellen und Nachweise

ORD-Eintrag
ord-af31975989c84987a67bbf305a6cd574
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466186B2

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