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

HRID 2246682Notes

Reaction equation

HRID 2246682 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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 62.2 was generated as a brown oil and used directly in the next step without further purification.

Workup

  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

Sources & evidence

ORD record
ord-52b9fac9a8e74665913d63fc0341a1f9
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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