N-bromobutanimide → 5-Bromo-2-(bromomethyl)benzonitrile

HRID 1921320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921320
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][Br:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 129940045-Bromo-2-methylbenzonitrile

Produkt 1

HCID 442031405-Bromo-2-(bromomethyl)benzonitrileAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-methylbenzonitrile (5.0 g, 25.5 mmol), N-bromosuccinimide (4.54 g, 25.5 mmol), 2′,2′-azobis(2-methylpropionitrile) (0.05 g) and carbon tetrachloride (25 mL) is heated at reflux for 75 min. After cooling to room temperature, the solids are removed by filtration. The filtrate is concentrated and the residue purified by chromatography eluting with cyclohexane-20% ethyl acetate. Product containing fractions are combined and concentrated to afford 5-bromo-2-bromomethylbenzonitrile (2.69 g, 38%). LC/MS: MS showed no parent molecular ion peak; RT 3.52 min.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 75 min
  3. customthe solids are removed by filtration
  4. concentrationThe filtrate is concentrated
  5. customthe residue purified by chromatography
  6. washeluting with cyclohexane-20% ethyl acetate
  7. additionProduct containing fractions
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-88b50ee940064fe38590d9e5f5760b69
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173682B2

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