Azobisisobutyronitrile → 3-(Bromomethyl)benzophenone

HRID 1890629

Reaktionsgleichung

Reaktionsgleichung von HRID 1890629
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 695113-Methylbenzophenone

Produkt 1

HCID 895863-(Bromomethyl)benzophenoneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Commercially available 3-methylbenzophenone (4.00 g, 20.4 mmol) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (4.71 g, 26.5 mmol) and 2,2′-azobisisobutyronitrile (1.00 g, 6.09 mmol) was added to the solution, followed by stirring at 75° C. for 6.5 hours. After the reaction mixture was cooled, the precipitates were filterd out. The filtrate was combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 3-bromomethylbenzophenone (4.31 g, yield 77%).

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-b75a6751a95049cb8d4a6eba42d81a6e
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507484B2

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