5-Fluoro-2-methylphenol → 3-Fluoro-6-methyl-2-nitrophenol

HRID 400595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400595
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.F[B-](F)(F)F.[O:15]=[N+:16]=[O:17]>C(#N)C.O>[F:1][C:2]1[C:7]([N+:16]([O-:17])=[O:15])=[C:6]([OH:8])[C:5]([CH3:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 27746165-Fluoro-2-methylphenolHCID 11073463Nitronium tetrafluoroborate

Produkt 1

HCID 600262953-Fluoro-6-methyl-2-nitrophenolAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred solution of 5-fluoro-2-methylphenol (640 mg, 5 mmol) in 20 mL of anhydrous acetonitrile was cooled to −30° C. to −40° C. and treated with nitronium tetrafluoroborate (740 mg, 5.5 mmol). After 45 minutes, the reaction mixture was diluted with 100 mL of cold water and extracted with three 50 mL portions of dichloromethane. The combined organic layers were washed with three 25 mL portions of water, dried over sodium sulfate, and concentrated in vacuo to give a reddish crystalline solid. Chromatography over SiO2 (5% ethyl acetate in hexanes) gave 0.58 g of the title product as bright yellow solid (68% yield).

Aufarbeitung

  1. extractionextracted with three 50 mL portions of dichloromethane
  2. washThe combined organic layers were washed with three 25 mL portions of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a reddish crystalline solid

Quellen und Nachweise

ORD-Eintrag
ord-837cc21af9e64e5591bc205f022366b6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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