Azobisisobutyronitrile → 4-Bromomethyl-2,6-dimethylnitrobenzene

HRID 1577144

Reaktionsgleichung

Reaktionsgleichung von HRID 1577144
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[CH3:12])([O-:3])=[O:2].[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:11][C:7]1[CH:8]=[C:9]([CH3:10])[C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH3:12])[CH:6]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 690512-Nitromesitylene

Produkt 1

HCID 205718604-Bromomethyl-2,6-dimethylnitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Nitromesitylene (20.0 g) is added to a mixture of N-bromosuccinimide (11.7g, 2 equivalents) and azobisisobutyronitrile (10 mg) in carbon tetrachloride (1000 ml). The flask is illuminated with a bright incandescent bulb (controlled by a Variac) with stirring until reflux occurs; an additional heat source is required. After 4 hours the reaction mixture is cooled, evaporated to a residue and partitioned between water and dichloromethane. The organic phase is separated, dried, and evaporated to a residue which is purified by column chromatography on silica gel by gradient elution: benzene/hexane (1:9 to 4:1). The purified product, mostly 4-bromomethyl-2,6-dimethylnitrobenzene, is isolated as an orange oil, 36.8 g.

Aufarbeitung

  1. customThe flask is illuminated with a bright incandescent bulb (
  2. temperatureuntil reflux
  3. temperatureAfter 4 hours the reaction mixture is cooled
  4. customevaporated to a residue
  5. custompartitioned between water and dichloromethane
  6. customThe organic phase is separated
  7. customdried
  8. customevaporated to a residue which
  9. customis purified by column chromatography on silica gel by gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-076af3ec3b964e09bf519a9a7b954d73
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04287201

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