N-bromobutanimide → 2-Bromo-4-(bromomethyl)benzonitrile

HRID 564440

Reaktionsgleichung

Reaktionsgleichung von HRID 564440
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][Br:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 8208022-Bromo-4-methylbenzonitrile

Produkt 1

HCID 534255212-Bromo-4-(bromomethyl)benzonitrileAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-4-methylbenzonitrile (13.3 g, 81.4 mmol), NBS (14.4 g, 84.4 mmol) and BPO (0.20 g) in CCl4 (150 mL) was heated for 4 h at reflux. The reaction mixture was cooled to room temperature and filtered. Then the solid was washed with CCl4 (20 mL×2) and the combined filtrate was washed successively with saturated sodium bicarbonate (50 mL), water (2×100 mL) and sodium thiosulfate (50 mL). The organic phase was dried over Na2SO4 and concentrated in vacuum afforded the titled compound, 2-bromo-4-(bromomethyl)benzonitrile (18.7 g, 100%).

Aufarbeitung

  1. temperaturewas heated for 4 h
  2. temperatureat reflux
  3. filtrationfiltered
  4. washThen the solid was washed with CCl4 (20 mL×2)
  5. washthe combined filtrate was washed successively with saturated sodium bicarbonate (50 mL), water (2×100 mL) and sodium thiosulfate (50 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8f7170bed54b4234af375a4e6fd956e9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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