Is it possible by any means or by using some reagents to convert hexane to 1,6-dibromohexane? The yield should also be good.
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3$\begingroup$ In case you need 1,6 disubstituted hexane, consider either a dirt cheap adipic acid as a starting material or coupling of two $\ce{C3}$ fragments, porduced from allilic derivatives. $\endgroup$ – permeakra Oct 20 '14 at 11:20
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In principle, alkanes may be converted to alkyl bromides by photoinitiated bromination.
However, taking statistics (2 $\ce{CH3}$ vs 4 $\ce{CH2}$ groups) and stabilities of the radicals resulting from H abstraction by a bromine radical from your starting material into account, this approach is pretty worthless and will most likely yield 1,6-dibromohexane as a minor product in a complex mixture.
Consequently, your reasonable options are a) a different starting material (and a different synthesis) or b) simply buy 1,6-dibromohexane (around 20 Euro for 100 g).
answered Oct 20 '14 at 10:14
