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6.1.38.16.2 Variation 2: Brominolysis

DOI: 10.1055/sos-SD-006-00903

Zaidlewicz, M.; Krzeminski, M.Science of Synthesis, (200561152.

The reaction of bromine with trialkylboranes, such as 62, in tetrahydrofuran in the dark is quite slow; however, it is greatly accelerated in the presence of base.[‌360‌] The use of sodium methoxide in methanol provides pure alkyl bromides in good yields. For example, 11-bromoundec-1-yl acetate [63, R1=(CH2)9OAc; R2=H][‌361‌] can be isolated in 97% yield (Scheme 105). Trialkylboranes with primary alkyl groups react with the utilization of all three alkyl groups. Consequently, hydroboration combined with methoxide-induced bromination of trialkylboranes provides a convenient procedure for the overall anti-Markovnikov hydrobromination of terminal alkenes. The procedure also accommodates functionalized alkenes, for example, unsaturated bromides and esters.

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References


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