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Chlorosafrole and the Finkelstein reaction
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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
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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
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http://rhodium.lycaeum.org/chemistry/halosafrole.txt
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-the good reverend drone
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