dormouse (Member)
04-19-00 15:53
No 122783
      Chlorosafrole and the Finkelstein reaction -rev drone  Bookmark   


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Author  Topic:   Chlorosafrole and the Finkelstein reaction 
rev drone
Member   posted 01-06-99 12:26 PM          
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Alledgedly, chlorosafrole is readily prepard via safrole, HCl, and a PTC. This is good, if it is the case. Does anybody have notes on this?
Chlorosafrole isn't as reactive as its heavier analogs bromo- and iodosafrole. However, I want to share with you all the magic of yet another phase-transfer catalylzed reaction: a variation of the Finkelstein reaction.

Yes, a little quaternary ammonium salt, a dash of CaBr2 (I've heard rumors NaBr works too), and a person can readily convert alkyl chlorides to bromides without breaking a sweat.

Synthesis 34, (1984)
J. Chem. Soc. Chem. Comm. 1250 (1986)
Isr. J. Chem. 26, (1985) 243

For those who prefer iodides:

US Pat. 3992432 (1976)
CA 72, 115271 (1970)
J. Chem. Soc. Chem. Comm. 879 (1974)
Synth. Comm. 16, (1986) 1029

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-the good reverend drone


Rhodium
Administrator   posted 01-06-99 04:38 PM          
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I have experimental details from runs using HCl/Aliquat 336 on safrole. Look in my Halosafrole doc at my page.
 
The Cook
Member   posted 01-14-99 12:04 AM          
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Amen Brother! (or sister!) Aliquat is funstuff!
So drone-are you going to try for a one-pot PTC? This might be your baby...
 
rev drone
Member   posted 01-14-99 09:11 AM          
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A one-pot-shot with this reaction would be the holy grail. I envision a three-step procedure:
1) PTC-catalyzed addition of HCl to safrole

2) PTC-catalyzed halogen exchange may not be necessary, but it could only help)

3) PTC-catalyzed amination

OF course, at each step, at least one of the phases would haver to be replaced and the other cleaned up, so I don't know if it truly qualifies as an OPS. Still, if it all could be done with aliquot 336, it just be the most amazing thing in the world.

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-the good reverend drone


ChemHack
Member   posted 01-14-99 07:33 PM          
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Hey Rhodium,
I double checked your page but didn't find anything about aqueous HBr and PTC. Didn't I read somewhere that bad things happen using this route?


rev drone
Member   posted 01-15-99 10:14 AM          
-------------------------------------------------------------------------------- http://rhodium.lycaeum.org/chemistry/halosafrole.txt 
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-the good reverend drone


rev drone
Member   posted 01-15-99 10:18 AM          
-------------------------------------------------------------------------------- http://rhodium.lycaeum.org/chemistry/halosafrole.txt 
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-the good reverend drone


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