Azobisisobutyronitrile → 6-Bromo-7-(bromomethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

HRID 731213

Reaktionsgleichung

Reaktionsgleichung von HRID 731213
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8]([CH3:14])([CH3:13])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15].C1C(=O)N([Br:24])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][Br:24])[C:8]([CH3:14])([CH3:13])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 100393466-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 234989536-Bromo-7-(bromomethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

The mixture of 6-bromo-7-methyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (4.20 g, 15 mmol), NBS (3.20 g, 18 mmol), 2,2′-azobisisobutyronitrile (0.3 g, 1.8 mmol) and CCl4 (120 mL) was heated at reflux for 16 hours. The mixture was concentrated under reduced pressure to about 50 mL. The reaction was then filtered, and the solid was washed with Et2O (20 mL). The combined organic solution was then concentrated under vacuum to generate crude product. Crude 91.2 was generated as a brown oil and used directly in the next step without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe mixture was concentrated under reduced pressure to about 50 mL
  4. filtrationThe reaction was then filtered
  5. washthe solid was washed with Et2O (20 mL)
  6. concentrationThe combined organic solution was then concentrated under vacuum
  7. customused directly in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-4d9162968f024969a493a6db5ba91605
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582803B2

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