Benzoyl Peroxide → 4-(4-Bromomethyl-3-chloro-phenoxy)-2-chloro-benzonitrile

HRID 2386835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2386835
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([Cl:18])[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[CH:12][C:13]=1[Cl:18]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 666970942-Chloro-4-(3-chloro-4-methyl-phenoxy)-benzonitrile

Produkt 1

HCID 666971204-(4-Bromomethyl-3-chloro-phenoxy)-2-chloro-benzonitrileAusbeute 17,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-chloro-4-(3-chloro-4-methyl-phenoxy)-benzonitrile (14.41 g) in CCl4 (100 ml) under argon were added N-bromosuccinimide (9.5 g) and dibenzoylperoxide (1.38 g). The mixture was heated to reflux for 2.5 h. After cooling to room temperature, the mixture was filtered. The filter cake was washed with cyclohexane. The combined filtrate was concentrated to dryness to give the crude product (19.75 g) as a light orange solid. Part of the product was purified by repeated chromatography (SiO2, cyclohexane/ethyl acetate 1:0=>4:1) to give the title compound as an off-white solid (3.27 g).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2.5 h
  3. filtrationthe mixture was filtered
  4. washThe filter cake was washed with cyclohexane
  5. concentrationThe combined filtrate was concentrated to dryness
  6. customto give the crude product (19.75 g) as a light orange solid
  7. customPart of the product was purified by repeated chromatography (SiO2, cyclohexane/ethyl acetate 1:0=>4:1)

Quellen und Nachweise

ORD-Eintrag
ord-20594c83bd074a62ad5677dec25c9fa0
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268820B2

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