m-Chloroperbenzoic acid → 2-Fluoro-4-(oxiran-2-yl)benzonitrile

HRID 1187013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187013
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[F:11][C:5]1[CH:4]=[C:3]([CH:1]2[CH2:2][O:20]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 219046072-Fluoro-4-vinylbenzonitrile

Produkt 1

HCID 552965762-Fluoro-4-(oxiran-2-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-ethenyl-2-fluorobenzonitrile (18.0 g, 122 mmol) in 200 mL of DCM was slowly added mCPBA (74.8 g, 367.347 mmol) in portions at 0° C. The mixture was warmed to room temperature and stirred overnight. The solution was washed with aqueous Na2SO3 until KI paper didn't change color. The organic layers was washed with brine and then concentrated. The residue was purified via column chromatography to give 2-fluoro-4-oxiran-2-ylbenzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.59˜7.62 (m, 1H), 7.12˜7.22 (m, 2H), 3.89˜3.91 (m, 1H), 3.20˜3.22 (m, 1H), 2.72˜2.74 (m, 1H).

Aufarbeitung

  1. customat 0° C
  2. washThe solution was washed with aqueous Na2SO3 until KI paper didn't change color
  3. washThe organic layers was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-19b82bdc934b46819cefe92112e9dc9a
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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