Azobisisobutyronitrile → HCID 59451576, Verbindung

HRID 1874783

Reaktionsgleichung

Reaktionsgleichung von HRID 1874783
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=2[F:19])[CH:9]=1)[C:5]#[N:6].C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:18][C:13]1[C:12]([F:19])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:5]#[N:6])[C:16]([Cl:17])=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimide2×HCID 594516403-Chloro-5-(6-chloro-2-fluoro-3-methylphenoxy)benzonitrile

Produkt 1

HCID 59451576HCID 59451576, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3-Chloro-5-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile (1.8 g, 6.1 mmol) was dissolved in CCl4 (200 mL). NBS (1.2 g, 6.7 mmol) and AIBN (0.63 g, 3.8 mmol) were added and the reaction mixture was placed in oil bath at 85° C. and stirred for 4 h. The reaction was monitored by TLC and more AIBN and NBS were added as necessary. The reaction was cooled, filtered and the solid washed with CCl4. The solvent was evaporated. Purification was accomplished by column chromatography (hexane/EtOAc eluent) to afford the title compound (1.8 g, 79%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.81 (s, 1H), 7.49-7.59 (m, 3H), 7.47 (d, 1H), 4.73 (s, 2H). GC-MS, 372.9 (M).

Aufarbeitung

  1. customthe reaction mixture was placed in oil bath at 85° C.
  2. additionwere added as necessary
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. washthe solid washed with CCl4
  6. customThe solvent was evaporated
  7. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-81e8ca9c30bc451ca73ed26f2a9a8f00
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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