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dormouse
(Member)
04-19-00 15:53
No 122783
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Chlorosafrole and the Finkelstein reaction -rev drone
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the Hive BB Serious Chemistry Forum Chlorosafrole and the Finkelstein reaction profile | register | preferences | faq | search next newest topic | next oldest topic Author Topic: Chlorosafrole and the Finkelstein reaction rev drone Member posted 01-06-99 12:26 PM -------------------------------------------------------------------------------- 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 ------------------ -the good reverend drone Rhodium Administrator posted 01-06-99 04:38 PM -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 safrole2) 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. ------------------ -the good reverend drone ChemHack Member posted 01-14-99 07:33 PM -------------------------------------------------------------------------------- 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 ------------------ -the good reverend drone rev drone Member posted 01-15-99 10:18 AM -------------------------------------------------------------------------------- http://rhodium.lycaeum.org/chemistry/halosafrole.txt ------------------ -the good reverend drone All times are CT (US) next newest topic | next oldest topic Administrative Options: Close Topic | Archive/Move | Delete Topic Hop to: Select a Forum or ArchiveList of Forums:General DiscussionAcquisition DiscourseChemistry DiscourseMethods DiscourseNovel DiscourseCrystal MethSerious Chemistry ForumThe Hive CouchSerious Tryptamine DiscourseAdmin Chill-out TentList of Archives:Couch ArchivesClassics!Law and OrderThe litter box.misc. PEAs
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