hms_beagle (Stranger)
05-27-02 14:02
No 314896
      4-bromotoluene and 4-methyl PCP  Bookmark   

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.  

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.

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?

05-27-02 20:13
No 315041
      Grignard reagent.  Bookmark   

Don`t know about PCP but you could make some really good cocaine anolouges with the grignard reagent derived from that bromo toulene.
05-28-02 15:17
No 315320
      ...bromination of Toluene will result in ...  Bookmark   

...bromination of Toluene will result in 2-Bromotoluene and 4-Bromotoluene.

05-28-02 18:05
No 315392
      2, bromo, 4, bromo  Bookmark   

4-bromo is what you want if you can seperate it from 2- bromo.
05-29-02 10:50
No 315660
      Chlorotoluene  Bookmark   

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.