Sciencemadness Discussion Board - phenethylbromide synthesis

phenethylbromide synthesis

tom haggen - 17-11-2005 at 21:05

Anyone? I looked around google a little bit and couldnt really seem to find anything. I assume one of your starting reagents would be ethyl bromide. What would be a good reagent to gain a phenyl group?

Antimarkonikov addition of HBr to Styrene

gsd - 18-11-2005 at 06:42

Beta - Bromo ethylbenzene can be synthesized by antimarkonikov addition of gaseous HBr to Styrene in presence of peroxide catalyst.

There are lots of references to this in std. organic chemistry texts.

[Edited on 18-11-2005 by gsd]

joe_aldehyde - 18-11-2005 at 11:48

is everybody gonna make fent now?

hydroboration of styrene and subsequent halogenation would be another possibility.

tom haggen - 18-11-2005 at 19:56

Am I that transparent?

Im trying to wrap my head around the nomenclature of this one. Could I say 1-bromo-2-phenylethane?

[Edited on 19-11-2005 by tom haggen]

joe_aldehyde - 19-11-2005 at 01:10

of course you could, and the name according to IUPAC would be 2-phenylethylbromide. i wonder, tho, why everybody is so excited about fent. i strongly suggest that you get as well-informed as you can before attempting the synthesis. this compound class seriously is nothing to blindly toy with.

>>>>>>>>>>>>>>>>>>>

AND CERTAINLY NOT TO SELL TO ANYONE TO MAKE PROFIT!

[Edited on 21-11-2005 by joe_aldehyde]

tom haggen - 6-12-2005 at 13:28

With regards to the synthesis. You say to use an antimarkonikov. Well isn't the carbocation going to form on the benzylic carbon because of the greatest stability?

[Edited on 6-12-2005 by tom haggen]

The_Davster - 6-12-2005 at 15:36

Not in this case, the peroxide(through a mechanism I am not familiar with) causes the anti-markovnikov addition of HBr across the double bond. Thus sticking the Br on the primary carbon

Joe_aldehyde, are you saying to use hydroboration to get the 2-phenolethanol, and then go to the 2-phenyl-1-bromoethane via what? Protonate the OH to OH2(+) and go SN2 from there to the 2-phenyl-1-bromoethane? Wouldent elimination reactions getting you back to styrene be a pain here?

EDIT: What is fent and why does everyone want it? I'm guessing its a drug of sorts?

[Edited on 6-12-2005 by rogue chemist]

carbene reaction conditions?

joe_aldehyde - 6-12-2005 at 16:11

Quote:

Originally posted by rogue chemist
Joe_aldehyde, are you saying to use hydroboration to get the 2-phenolethanol, and then go to the 2-phenyl-1-bromoethane via what? Protonate the OH to OH2(+) and go SN2 from there to the 2-phenyl-1-bromoethane? Wouldent elimination reactions getting you back to styrene be a pain here?

R-OH + PBr3 -> R-Br
or
R-OH + SOCl2 -> R-Cl

[Edited on 7-12-2005 by joe_aldehyde]

sparkgap - 6-12-2005 at 19:42

rogue chemist, "fent" is the street shorthand for the potent opiate fentanyl.

I'd understand why joe_aldehyde was very wary... it takes only a small dose to act, and only a bit larger to kill. It's Schedule II in the U.S., IIRC.

sparky (~_~)

enima - 7-12-2005 at 13:48

yes, its an extremely potent, highly addictive opiate (more so than heroine). Its active at 1mg.

It is kinda scary.

New fentanyl epidemic

prole - 26-5-2006 at 11:32

It seems someone out there in Clandestine Chemistry Land has whipped up a batch of fentanyl and thought distributing it would be a good idea... http://www.freep.com/apps/pbcs.dll/article?AID=2006605260330

Please, those so inclined, keep this shit at home.

triphenylphosphineoxide - 27-5-2006 at 05:27

Just to give an idea of how dangerous fentanyl can be, it was used by the Spetznaz to end the Moscow theatre siege in 2002.
Before storming the theatre the russian special forces pumped fentanyl into the building. 140+ people died mostly as a result of respiratory failure due to the fentanyl. Of the 120 civilians killed 119 died as a result of fentanyl.

dr. nick - 9-9-2006 at 01:46

was told phenethylbromide can also be produced by reaction of beta-phenetylamine and sodium bromide, but can not reconstruct this -
can someone approve or negate that?
If so, how?

btw: phenetylbromide can also be used for synthing levorphan.
you see, one can also have honarable causes besides fent wanting to produce it
...