Azobisisobutyronitrile → 4-(Bromomethyl)-1-chloro-2-methoxybenzene

HRID 17905

Reaktionsgleichung

Reaktionsgleichung von HRID 17905
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 993521-Chloro-2-methoxy-4-methylbenzene

Produkt 1

HCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzeneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57.2 g, 0.32 mol) and AIBN (10 g, 60 mmol). The mixture was heated at reflux for 3 hours. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (Petroleum Ether/EtOAc=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was evaporated under vacuum
  4. customthe residue was purified by column chromatography on silica gel (Petroleum Ether/EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-127a3157d14c402ba00add575389526d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741321B2

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