Benzoyl Peroxide → (3-Bromo-3-phenylpropoxy)(tert-butyl)dimethylsilane

HRID 451490Notes

Reaction equation

HRID 451490 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10083485Tert-butyldimethyl(3-phenylpropoxy)silane

Product 1

HCID 67335370(3-Bromo-3-phenylpropoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of tert-butyldimethyl(3-phenylpropoxy)silane (2.22 g, 8.86 mmol), N-bromosuccinimide (1.58 g, 8.86 mmol) and benzoyl peroxide (66.4 mg, 266 μmol) in carbon tetrachloride (17.8 mL) was heated to reflux for 3 hours. The reaction was filtered, the precipitate washed with carbon tetrachloride and the solvent was evaporated. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow oil (1.63 g, 55%) after column chromatography on silica gel using heptane/ethyl acetate 19:1 (v/v) as eluent. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.42-7.26 (m, 5H), 5.42 (dd, 1H), 3.76 (m, 1H), 3.68 (m, 1H), 2.48 (m, 1H), 2.28 (m, 1H), 0.90 (s, 9H), 0.06 (s, 3H), 0.03 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe reaction was filtered
  4. washthe precipitate washed with carbon tetrachloride
  5. customthe solvent was evaporated
  6. additionWater was added
  7. extractionthe reaction was extracted twice with diethyl ether
  8. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-adf8ea6fa3bf4ff4ad7f77e4ab8d39c9
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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