I am refluxing $\ce{HBr}$ with 1,6-hexanediol for 16 hours at $80\ ^\circ\mathrm{C}$ in toluene. How can I be sure that more than $90\,\%$ of the product is brominated only at one terminal? If the amount of double brominated product is in more than $10\,\%$ of the total yield, then the product mixture will be useless for me.
In an article by Katharina C. Kress, Martin Kaller, Kirill V. Axenov, Stefan Tussetschläger, and Sabine Laschat, published in Beilstein J. Org. Chem., 2012, 8, 371-378 (DOI), this procedure is described. From the Supporting Information, I read that the authors obtained the product in 72% yield after
column chromatography on silica gel (hexanes/EtOAc, 1:1)
I wouldn't be astonished if that's as good as it can get.
${}^\circ$
. $\endgroup$ – Martin - マーチン♦ May 22 '15 at 4:12