Bromtrimethylsilan

VerwendenBromotrimethylsilane is a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers; effective reagent for formation of silyl enol ethers; can function as brominating agent.Amines react with TMS-Br to form isolable adducts, which react readily with ketones to form enamines under mild conditions (eq 15).

synthetischealthough many methods are reported, only a few are provided here: chlorotrimethylsilane undergoes halogen exchange with either magnesium bromide in Et2O or sodium bromide in MeCN, which allows in situ reagent formation (eq 1); alternatively, hexamethyldisilane reacts with bromine in benzene solution or neat, to afford only TMS-Br with no byproducts (eq 2).4 TMS-Br may also be generated by reaction of hexamethyldisiloxane and aluminum bromide (eq 3).However, it should be noted that the reactivity of in situ generated reagent appears to depend upon the method of preparation.