Benzoyl Peroxide → [2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane

HRID 1172463Notes

Reaction equation

HRID 1172463 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:19]([Si:23]([CH3:33])([CH3:32])[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])([CH3:22])([CH3:21])[CH3:20].[Br:34]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl>[Br:34][CH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 11310617tert-Butyl-dimethyl-o-tolyloxy-silane

Product 1

HCID 13594450[2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A catalytic amount of benzoylperoxide (0.5 g) was added to a refluxing solution of an equimolar mixture of Example 1d (30 g, 0.134 mol) and N-bromosuccinamide (24 g, 0.134 mol) in dry CCl4 (175 mL) for 1.5 h. The reaction mixture was filtered, concentrated and purified using flash chromatography (silica gel, PE60-80° C.) to obtain the title compound as an oil. Yield: 36 g, (90%); 1H NMR (CDCl3): δ 0.30 (s, 6H, 2CH3), 1.10 (s, 9H, 3CH3), 4.5 (s, 2H, CH2), 6.8-7.5 (m, 4H, Ar).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified

Sources & evidence

ORD record
ord-2db2e60d675040e6b078bc16b7f38483
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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