Benzoyl Peroxide → (3-(Bromomethyl)phenyl)trimethylsilane

HRID 1938574Notes

Reaction equation

HRID 1938574 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][Si:2]([CH3:10])([CH3:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][Br:12]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10866684Trimethyl(M-tolyl)silane

Product 1

HCID 12583977(3-(Bromomethyl)phenyl)trimethylsilane

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-trimethylsilyltoluene (3.28 g, 10 mmol), N-bromosuccinimide (1.78 g, 10 mmol) and benzoylperoxide (10 mg) in CCl4 (20 ml) was stirred under reflux for 3 hours, then cooled and filtered. The solvent was removed under reduced pressure and 3-trimethylsilylbenzylbromide was purified by distillation.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure and 3-trimethylsilylbenzylbromide
  5. distillationwas purified by distillation

Sources & evidence

ORD record
ord-51497a61883e44c8b841f8ccf3198710
Source dataset
uspto-grants-1997_12
Patent number
US05693668

Reaction notes

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