Water → 3-Bromo-2-fluoro-5-nitrobenzonitrile

HRID 389466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389466
N[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([Br:13])=[C:6]([F:14])[C:3]=1[C:4]#[N:5].N(OC(C)(C)C)=O.O>O1CCCC1>[Br:13][C:7]1[C:6]([F:14])=[C:3]([CH:2]=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=1)[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 86662399HCID 86662399, Verbindung

Produkt 1

HCID 667600553-Bromo-2-fluoro-5-nitrobenzonitrileAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a cooled (0° C.) solution of 2-amino-5-bromo-6-fluoro-3-nitro-benzonitrile (8.0 g, 30.8 mmol) in tetrahydrofuran (40 mL) was added tert-butyl nitrite (4.6 mL, 37 mmol) dropwise and stirred for 16 h at 50° C. The reaction mixture was treated with water and extracted with ethyl acetate. The organic fraction was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (2% to 10% ethyl acetate:hexanes) afforded 4.0 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.72 (dd, J=3.0, 2.7 Hz, 1H), 8.51 (dd, J=3.0, 2.7 Hz, 1H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic fraction was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (2% to 10% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1939ce7545e848309d9de087f932eb13
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378104B2

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