Benzoyl Peroxide → Trimethylsilyl-4-bromocrotonate

HRID 1246289Notes

Reaction equation

HRID 1246289 reaction equation
[CH3:1][Si:2]([O:5][C:6](=[O:10])/[CH:7]=[CH:8]/[CH3:9])([CH3:4])[CH3:3].[Br:11]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]([O:5][C:6](=[O:10])/[CH:7]=[CH:8]/[CH2:9][Br:11])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5702560Trimethylsilyl crotonate

Product 1

HCID 12730183Trimethylsilyl-4-bromocrotonateYield 65%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
77 °C

Procedure

A stirred mixture of trimethylsilylcrotonate (131 g, 0.828 mol), N-bromosuccinimide (206 g, 1.16 mol), benzoyl peroxide (3.41 g, 0.141 mol) and carbon tetrachloride (1 L) is warmed to reflux (77° C.) under visible light for 5 hours. The mixture is cooled to room temperature and the precipitated solid is removed by filtration. The filtrate is concentrated to a residue, which is distilled under reduced pressure. The product fractions are collected at 93–106° C. (9–15 mmHg) to give 127 g of the title compound (65%). GC-MS purity is 83–89%, 1HNMR is consistent with expected structure.

Workup

  1. temperatureis warmed
  2. temperatureThe mixture is cooled to room temperature
  3. customthe precipitated solid is removed by filtration
  4. concentrationThe filtrate is concentrated to a residue, which
  5. distillationis distilled under reduced pressure
  6. customThe product fractions are collected at 93–106° C. (9–15 mmHg)

Sources & evidence

ORD record
ord-b2fbe36681bc41c2a243f0d6707605d6
Source dataset
uspto-grants-2006_10
Patent number
US07126025B2

Reaction notes

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