Benzoyl Peroxide → 1-(1-Bromoethyl)-4-(trimethylsilyl)benzene

HRID 1768561Notes

Reaction equation

HRID 1768561 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1)[CH3:2].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:1]([C:3]1[CH:8]=[CH:7][C:6]([Si:9]([CH3:10])([CH3:12])[CH3:11])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 280168(4-Ethylphenyl)(trimethyl)silane

Product 1

HCID 189488471-(1-Bromoethyl)-4-(trimethylsilyl)benzeneYield 91%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The product of Step A (59 g, 0.33 mole) was dissolved in carbon tetrachloride (700 mL). To this solution was added N-bromosuccinimide (59 g, 0.33 mole) and benzoyl peroxide (ca. 200 rag) in one portion. The reaction mixture was heated to reflux for 2.5 hours while being irradiated with a 275 watt sunlamp. After cooling, the solid succinimide was removed by filtration and the filtrate was washed with saturated aqueous NaHSO3. Drying (MgSO4) and concentration gave an oil (77 g, 91% yield) which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. customwhile being irradiated with a 275 watt sunlamp
  4. temperatureAfter cooling
  5. customthe solid succinimide was removed by filtration
  6. washthe filtrate was washed with saturated aqueous NaHSO3
  7. customDrying
  8. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-e41c25baefde4f14adf9090dc61d831a
Source dataset
uspto-grants-1995_01
Patent number
US05378708

Reaction notes

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