Benzoyl Peroxide → Trimethylsilyl-4-bromocrotonate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence