Azobisisobutyronitrile → 1-(Bromomethyl)-3,5-di-tert-butylbenzene

HRID 2210701Notes

Reaction equation

HRID 2210701 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)[CH2:15][Br:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 848193,5-Bis(tert-butyl)toluene

Product 1

HCID 44475071-(Bromomethyl)-3,5-di-tert-butylbenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3,5-Di-t-butyltoluene (5 g), N-bromosuccinimide (4.79 g) and azobisisobutyronitrile (20 mg) were dissolved in carbon tetrachloride (30 ml) and the solution was heated at reflux for 3 h. When cool, a white solid was removed by filtration, and the filtrate was concentrated yielding a yellow oil, which was used without further purification. 1H NMR (360 MHz, CDCl3) δ1.30 (18H, s, CH3), 4.45 (2H, s, CH2), 7.2 (2H, d, J=1.75 Hz, ArH), 7.4 (1H, s, ArH).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 3 h
  3. temperatureWhen cool
  4. customa white solid was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customyielding a yellow oil, which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-151601578adb40b0a289cee156a94df1
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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