Author Topic: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)  (Read 340 times)

jon

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a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« on: June 15, 2010, 05:20:32 PM »
after doing some research i found this paper.
it's a zinc/ammonium chloride system and it's solvolyzed by thf.
this reduction is high yeilding, works best on highly activated aromatic (the indole nucleus of bromocryptine and loperamide serve as good examples)
uses easy to obtain materials, reacts under very mild conditions (room temperature), is done is 15 minutes, and is highly chemoselective.

for your reading pleasure

Naf1

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #1 on: June 17, 2010, 02:10:31 AM »
Nice find! I can see where this is going, are we going to get a write-up?

jon

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #2 on: June 17, 2010, 02:17:34 AM »
i'm still outta service but the find was so appealing a personal friend of mine is eager to try it and i'll get the notes.

Vanadium

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #3 on: June 18, 2010, 01:47:43 AM »
For some reason I can't get the paper from the site; would somebody mind uploading it to a filesharing site and posting the link here?

Edit: Funny, it works now. Oh well; hope this isn't an irrelevant post now that I have the paper. :P
« Last Edit: June 19, 2010, 09:47:01 PM by Vanadium »

Sedit

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #4 on: June 18, 2010, 04:38:00 AM »
Wow, Dichlorobenzene to good ol' benzene anyone?

The large excess of Zn appears prohibitive but much can be recycled just making extra bulk to deal with.

What is the reasoning for the THF usage? Does it act only as a solvent or can substitution be made? It would be hard to find another water miscible ether solvent though but the slight solubility of Et2O in H2O might facilicate the reaction abit.
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jon

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #5 on: June 18, 2010, 09:46:12 PM »
thf is indipsensible maybe dioxolane would substitute it but you need the lone pairs on that oxygen to solvate organozinc compounds as they form complexes

rhodopsin

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #6 on: July 26, 2010, 04:01:35 PM »
would this work on 4-flouro-amphetamine?

Tsathoggua

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #7 on: July 26, 2010, 05:29:28 PM »
I doubt it, fluorine-carbon bonds are another beast entirely than your standard halides, and are nigh on impossible to split chemically due to fluorines crazy ass electronegativity.
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jon

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #8 on: July 27, 2010, 03:46:01 AM »
i did some research because the achille's heel is the qauternary double bond of the ergoline nucleus.
this indicates that it respects double bonds and many other functional groups.

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java

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #9 on: July 27, 2010, 06:01:16 PM »
...i think i will try it on a iodated former primary amino alcohol, see if it works .....java
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shroomedalice

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Re: a kitchen friendly means of dehalogenating aryl halides (bromocryptine eg:)
« Reply #10 on: August 22, 2010, 10:19:58 AM »
nitroethanol ha :)

will this work for non aryl halides