The Vespiary

The Hive => Novel Discourse => Topic started by: hms_beagle on May 27, 2002, 02:02:00 PM

Title: 4-bromotoluene and 4-methyl PCP
Post by: hms_beagle on May 27, 2002, 02:02:00 PM
I'd really like to know about the activity of 4-methyl PCP. It would be easy to synth from 4-bromo toluene, which itself could be made by bromination of toluene. I've looked into OTC prep of 4-bromotoluene, but I can't get hold of what seems to be the most promising paper:

Monobromination of aromatic rings using potassium bromide-sodium nitrate mixture in sulfuric acid.  
J. Chem. Soc. Pak.  (1992),  14(3),  212-14.  CODEN: JCSPDF  ISSN: 0253-5106.  Journal  written in English.  

Abstract
A simple and rapid method for the selective monobromination of arom. rings involving the use of a mixt. of potassium bromide and sodium nitrate in sulfuric acid (60% vol./vol.) is described.  Thus, PhMe was brominated by this method to give 70% 4-BrC6H4Me.
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It should be fairly easy to seperate any o-bromo toluene produced as a byproduct due to the differing melting points of the isomers. But I'd like to know the specific reaction conditions if possible. I don't suppose anyone has access to this journal and be willing to find out?

Title: Grignard reagent.
Post by: SPISSHAK on May 27, 2002, 08:13:00 PM
Don`t know about PCP but you could make some really good cocaine anolouges with the grignard reagent derived from that bromo toulene.
Title: ...bromination of Toluene will result in ...
Post by: Xicori on May 28, 2002, 03:17:00 PM
...bromination of Toluene will result in 2-Bromotoluene and 4-Bromotoluene.

mfg
Title: 2, bromo, 4, bromo
Post by: SPISSHAK on May 28, 2002, 06:05:00 PM
4-bromo is what you want if you can seperate it from 2- bromo.
Title: Chlorotoluene
Post by: psychokitty on May 29, 2002, 10:50:00 AM
Don't know about the isomers but according to the literature, chlorotoluene can be made OTC by reacting toluene with aqueous sulfuric acid and TCICA (trichloroisocyanuric acid).  The synthesis is supposedly easy to carry out.