[opsomath]

Hi all,

I am motivated to convert an alkene into an R-CH2-CH2-Br group! This is a stock reaction from Organic 1, of course, but the trouble is that it's actually hard to do. Vogel's has a procedure that uses HBr from a cylinder or generates it in situ from a bromination, but that is obnoxious. Has anyone developed a procedure which uses a bromide salt or anything handy like that? A bit of searching has not turned up anything. Thanks!

[Babcock_Hall]

You could add water in an anti-Markovnikov sense, then convert to the alkyl bromide.  I agree that a one-step procedure would probably be more convenient.

[discodermolide]

Why not hydroborate/oxidise to the alcohol and convert that to the bromide?
See also Wilger, D. J., Grandjean, J.-M. M., Lammert, T. R., & Nicewicz, D. A. (2014). The direct anti-Markovnikov addition of mineral acids to styrenes. Nature Chemistry, 6(, 720–726. http://doi.org/10.1038/nchem.2000

for additional references.

[opsomath]

Thanks for the Nat Chem paper, that's a good one.