Re: ORGLIST: selenium doixide oxidation

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From: Maringanti Krishna (maringanti9$##$
Date: Sat Nov 20 2004 - 01:31:08 EST

Dear Abhilash:
You should be able to MonoBrominate your methyl group with NBS in dichloromethane, and a catalytic amound of benzoyl peroxide or 500W lamp. If you dont have this stuff, just do the reaction in sunlight.Nothing happens to Cyano group under these conditions.
Then you carryout either Sommlet oxydation or treat the monobromide with DMSO. (DMSO is better).
Another method to oxydize your methyl group is to treat your methyl-cyanobenzene with n-BuLi-TMEDA complex at -78 degrees and dry buble air. Quenching the reaction mixture with aq. sodium sulfite will give your alcohol. then do PCC oxydation.
But why all this circus?
It I were you, I would see if I can buy it from Tokyo Kosei or any other source. If it is impendingly urgent, I will run reactions in parallel with different alternatives:
A better method to prepare your aldehyde will be to start from o-salicylaldehyde. Simple protection of -CHO, converting acid to amide- and POCl3 treatment-deprotection should give you the compound.
Or you could take up 2-Bromobenzaldehyde- make it an acetal and treat it with Copper Cyanide or even Zinc cyanide.
Good Luck!
Dr. M. Krishna
Senior Scientific Officer
Medicinal Chemistry Division
GVK Biosciences
ICICI Kowledge Park, Turkapalli
Tel: +91-40-23480050/60 ext-216
       +91-9849637251 (mobile)
Fax: +91-40-23480080
E-Mail: mkrishna$##$


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