ORGLIST: bromination of substituted pyridine

Date view Thread view Subject view Author view Attachment view

From: philip cherian (philip_189$##$yahoo.com)
Date: Wed Jul 26 2006 - 15:07:50 EDT

Hello everybody, i am trying to brominate the methyl group of 2-(piperazine)-6-methyl-pyridine-4-carboxylic acid using NBS in EtOAc under microwave conditions. (112C, 10mins). However, instead of the side chain bromination, i am getting nuclear monobromination at the 3 or 5 (major pdt,85% yield) and also the dibromo pdt. {Probably due to the o,p directing nitrogen of piperazine}. Any suggestion, ideas as to how to brominate this benzylic methyl selectively?
   

                 
---------------------------------
Groups are talking. We´re listening. Check out the handy changes to Yahoo! Groups.


_______________________________________________
ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ: http://www.orglist.net
To post a message (TO EVERYBODY) send to everybody$##$orglist.net
To unsubscribe, send to everybody-request$##$orglist.net the message: unsubscribe your_orglist_password your_address

Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Tue Feb 13 2007 - 14:17:01 EST