Sciencemadness Discussion Board

Isoamyl bromide from isopropanyl bromide?

Assured Fish - 17-7-2017 at 21:05

Is it possible to carry out an electrophilic addition reaction between isopropyl bromide and ethylene?
I figured that the carbon adjacent to the bromide is not electrophilic enough to attack the alkene but could it be accomplished with a catalyst, if so what catalyst?
isoamyl bromide.png - 1kB
If this is a retarded question which will not work at all then feel free to throw it in detritus or delete it.

Metacelsus - 18-7-2017 at 03:54

I doubt that route is feasible. Even if you could get the reaction to work, it would be hard to stop it after the addition of just one ethylene molecule, so you would get a mixture of various oligomers.

Assured Fish - 18-7-2017 at 14:59

Damn, this compound has annoyed me for quite some time, the only plausible easily accessible route to its synthesis that i can come up with is reacting isobutyl magnesium bromide with anhydrous formaldehyde gas or some very dry paraformaldehyde in a grignard reaction. Isobutyl bromide could be prepare from isobutyl nitrite which is sold as an OTC recreational inhalant in some countries.