Azobisisobutyronitrile → (4-Bromo-3-bromomethyl-phenoxy)-tert-butyl-dimethyl-silane

HRID 1049484Notes

Reaction equation

HRID 1049484 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][C:3]=1[CH3:16].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(OCC)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:8])[CH3:9])=[CH:4][C:3]=1[CH2:16][Br:17]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 17984598(4-Bromo-3-methylphenoxy)(tert-butyl)dimethylsilane

Product 1

HCID 19437125(4-Bromo-3-bromomethyl-phenoxy)-tert-butyl-dimethyl-silaneYield 30.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-bromo-3-methylphenoxy)(tert-butyl)dimethylsilane (6.97 g) and N-bromosuccinimide (6.21 g) in ethyl acetate (100 mL) was added 2,2′-azobis(isobutyronitrile) (383 mg), and the mixture was refluxed for 17 hr. The mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.65 g) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 17 hr
  2. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3757b5f31c3541aba121606f57cb3e81
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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