De-Bromination

[DrP]

Hi, if you have a brominated hydrocarbon - how easy/what can you do to de-brominate this (back to the hydrocarbon)? Can this be done via some sort of ion exchange column?

 

Cheers,

 

P.

[YT2095]

Nucleophilic substitution should do the trick

[big314mp]

You can't do an ion exchange column because the bromine won't dissociate off of the the rest of the organic molecule, the way it would in a salt. Therefore, you don't have any ions to exchange.

 

YT (I think) is referring to something like LiAlH4, which will react as if it is H-. It will act as a strong nucleophile.

 

Just for my own amusement, you can also eliminate to form the double bond, and then hydrogenate.

[YT2095]

this will also give you a better idea: http://en.wikipedia.org/wiki/Nucleophilic_substitution

[John Cuthber]

Convert it to a Grignard reagent then electrophilic substitution of "MgBr+" by H+

[big314mp]

Convert it to a Grignard reagent then electrophilic substitution of "MgBr+" by H+

 

I think I did this once.

 

Entirely unintentionally, of course

[DrP]

OK - Thanks for your comments and ideas. I thought this would be the case. I think I'm looking for something that doesn't exist - I want to be able pass a brominated hydrocarbon (12-15 chains long) over/through some kind of column or catalytic converter type thingy and return it to standard kerosene without too much fuss. I'm not sure if this is possible with the ease I am after.