Azobisisobutyronitrile → 1-(Bromomethyl)-3-methoxy-5-methylbenzene

HRID 1016781

Reaktionsgleichung

Reaktionsgleichung von HRID 1016781
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 701263,5-Dimethylanisole

Produkt 1

HCID 5855341-(Bromomethyl)-3-methoxy-5-methylbenzeneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A suspension of 3,5-dimethylanisole (13.60 g, 100 mmol), N-bromosuccinimide (18.35 g, 100 mmol) and 2,2′-azobis(2-methylpropionitrile) in CCl4 was heated under reflux for 1 h. The succinimide was filtered off, the filtrate was concentrated and the residue was chromatographed (SiO2, CH2Cl2/hexane 1:4). There were obtained 14.61 g (68%) of 1-bromomethyl-3-methoxy-5-methyl-benzene.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. filtrationThe succinimide was filtered off
  4. concentrationthe filtrate was concentrated
  5. customthe residue was chromatographed (SiO2, CH2Cl2/hexane 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-5950e910d8d348e4a9eda78d3c816990
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06476264B2

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