R-Cl + K-Phtalamide --> R-Phtalamide + KCl
R-Phtalamide + 2H2O --> R-NH2 + Phtalic acid
Seems pretty do-able, will be in the library this afternoon to look up K-phtalamide.
All the info you got on this is very much appreciated.
And for the R-Cl: isn't it easier to make not-chlorosaffy from saf with HCl/PTC ? I believe Chem Guy has info on this.
PS I couldn't check my hushmail yet (slow thing using older netxplorers)
Osmium replied to it a few times.
All the info I have on this is what I've posted here. I've just seen it in two books I've bought to learn general org. chem. They do not deal with special things so this can only be a hint into the right direction.
I don't know at all, if it works. I don't have a lab, sadly. But I know that to replace a secondary halogen you need a good nucleophile. I know NH3 is just a so-so nucleophile. And I know that the most expensive of my books sez K-phtalimide is a very good nucleophile. So all I can do with this info is combinig it and say: "Why not give it a try, the theory looks good". I also still have no library access but I will have in 2 weeks. I hope then I can give/get more refs and such.
Im not very up to date when it comes to Cl/Br/I-Safrole but have a look at this:
Al2O3 with H2O on it's surface + COBr2 -->
Al2O3 with HBr on it's surface + CO2
(also works with SiO2 and PI3/SOCl2)
this Al2O3 with HBr on it's surface reacts with alkenes to the halo-alkane with CH2Cl as solvent in 20min and 99% yield.
Here's the ref: Kropp, P.J., K.A. Daus, M. W. Tubergen, et al., J. Am. Chem. Soc., 1993, 115, 3071. Surface-mediated reactions. 3. Hydrohalogenation of alkenes.
Have fun and please report any dreams you may or may-not have dreamt.
--psyloxy--
Al2O3 is pretty easy to obtain. If the reaction can proceed with 48% HBr on the Al2O3 this is a huge improvement on the procedure that requires 7 days to halogenate with 48% HBr.
CHEM GUY: I suggest reading the ref. I for my part have no clue on the whole thing.
--psyloxy--
Also, element 109...
You are talking about the addition of HCl to safrole (or the like) with a Quarterny Ammunium Salt. I don't remenber talking about that recently. I think the last time I posted about that specificly was at least a year ago. I don't really have a lot of info on that specifically, but I'll try to answer any questions you have about it.
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--psyloxy--
How much Q-A-S is added per quantity of HCl ?
Is it just left at RT ? How long ? Yield ?
If you could answer any of these questions i would very much appreciate it.
Psyloxy: i look up K-phtalimide in the Merck but it only lists phtalimide and K-diphtalate
How would phtalimide add the the Cl/Br/I ?
--psyloxy--
Sorry if these questions sound stupid, but i want to understand first before i start dreaming things.
The problem here is that you need a saturated solution of HX in CH2Cl2. There can be water, but the article suggests that the water should be minimal or none exsistant.
The advantage is that you can use HCl which is much easier to get than HBr or HI. Disadvantage is that you should keep the water content very low.
BUT, since the aluma and silica are added as anhydrous one might beable to get away with a larger excess of aluma and or silica to get rid of some of the accidental water content. Alas, straight muractic acid won't work, but one could always add NaCl into a pop bottle of muractic acid and use the HCl gass that evolves to pump into a CH2Cl2 solution.
I wounder if CHCl3 would work in place of CH2Cl2?