Acid chlorides bromotrimethylsilane

Acid bromides.1 Acid chlorides can be converted to acid hromidcs by, reaction with bromotrimethylsilane (75 -95% yield). Acid iodides can be obtained by use of lodotrimethylsilane. 

Cleavage of lactones and carbonates. Lactones and carbonates react with bromotrimethylsilane to afford bromocarboxylic acid derivatives (equation I) and bromohydrin trimethylsilyl ethers (equation II), respectively acyclic, aliphatic esters do not react with bromotrimethylsilane. lodotrimethylsilane reacts in an analogous fashion with lactones, but in reaction with ethylene carbonate the main product is 1,2-diiodoethane (equation III). The >-bromocarboxylate derivatives are converted into acid chlorides by reaction with SOCL (equation I). 

Chlorotrimethylsilane can be added to alkenes to give alkyl chlorides. 1-Hexene reacts with MesSiCl in water to give 2-chlorohexane. Treatment of an alkene with KHF2 and SLF4 leads to the alkyl fluoride, and bromotrimethylsilane adds to alkynes to give the vinyl bromide. Trichloroisocyanuric acid reacts with terminal alkenes in water to give the 1-chloro alkane. ... 

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