Just so that you know, the first (and the second too) home-made 2C-B has been biotested by both SWIAntoncho and SWIVitsh a few days ago, so it already is no longer a dream The yields were shitty though so for a formal write-up to appear on the Hive we'll have to wait.
Antoncho/Vitsh..shit..how..fortuitous..
u both beat me to it
you see
MG is hoping to be
#3
with home-made 2C-B
I can't wait to read your bio assay results!
Just two questions:
Did u use Zn/HCl for final redn ?
How did u crystallize 2C-H (gassing or IPA/HCl) ?
[I know u will be posting a write-up later but this very morning tears of pity welled up in my eyes as I gazed upon lovely sunny powder* that begged me to relieve it of it's oxygen...& I hate to see anything suffer.. ;) ]
*I'm just assuming it's 2,5-DMNS cos if it ain't...well..fuck I hope it is..
Mountain Boy
hmmmmmmm would a catalytic alkylation similar to the one detailed in http://www.orgsyn.org/prep.asp?prep=cv6p0897 (http://www.orgsyn.org/prep.asp?prep=cv6p0897)
but using 2,-5-dimethoxybenzyl bromide + MeCN work here? Or does this only work with phenylacetonitriles?
Possibly glyme or diglyme?
see
http://www.ferro.com/our+products/industrial+specialties/products+and+markets/glycol+diethers/default.htm (http://www.ferro.com/our+products/industrial+specialties/products+and+markets/glycol+diethers/default.htm)
When all you've got is a nailgun, every problem looks like a messiah...
The formation of arynes from aryl halides by reaction of potassium t-butoxide with aryl halides.(4)
The formation of arynes from aryl halides by reactions with amide and substituted amide ions is well known, and it has been reported that a similar elimination of hydrogen bromide from bromobenzene can be effected in dimethyl sulphoxide by potassium t-butoxide.(1) Use of t-butyl alcohol instead of dimethyl sulphoxide led to a much slower reaction to give a much lower yield (35%). Complications arising from interaction of the aryne with the solvent also occur in the amide reactions.(2),(3) In connection, with another investigation, a route to arynes not involving reactive solvents, such as ammonia, dimethyl sulphoxide, or t-butyl alcohol, was required.
Arynes can be produced conveniently by reaction of an aryl halide, usually the bromide, although chlorides also react, with potassium t-butoxide alone, such reactions being effected either in an excess of the halide at an elevated temperature or, more conveniently, in boiling t-butylbenzene as solvent.
Experimental:
Bromobenzene:
Bromobenzene (46,7g) and potassium t-butoxide (4,093g) were boiled under reflux for 4 hr. The precipitated potassium bromide was filtered off and the filtrate examined by g.l.c. (10% SIL, 140°) ; this showed a product peak with a retention time relative to bromobenzene of 1,63. A sample of the product was obtained by preparative g.l.c. (20% PPE, 150°) ; i.r. and H n.m.r. spectra were consistent with formulation of the product as phenyl t-butyl ether. The yield was 92% based on potassium t-butoxide.
The yields are in the range of 80-70 % for the bromo benzene o,m, or p substituted with Me or OMe
I think that acetonitrile is a better nucleophile than the formed HO-tBu, and so phenylacetonitrile will form if some CH3CN is put in it but it appear that this reaction require elevated temperature, t-butyl benzene boil at 169°C and CH3CN at 80°C, so I don't know it this will work without an autoclave?
FUCK IT, I prefer the ref in DME, sad that sodium amide is such a pain in the ass to make >:( :( ! But I think that I will still play with ammonia.... ::) or maybe with di-isopropylamine like Antoncho said in post Post 381200 (https://www.thevespiary.org/talk/index.php?topic=11321.msg38120000#msg38120000)
(Antoncho: "Alkali metal amides: strong basses for the masses!", Novel Discourse)
Ref:
(1) D. J. Cram, B. Rickborn, and G. R. Knox, J. Amer. Chem.
Soc., 1960, 82, 6412.
(2) D. J. Cram and A. C. Day, J. Org. Chem., 1966, 31, 1227.
(3) M. Kise, T. Asari, N. Furukwa, and S. Oae, Chem. and Ind.,1967, 276.
(4) J Chem Soc 196?(7,8,9?) p 1860