From: JSM (jaininder2002$##$yahoo.com)
Date: Tue Oct 15 2002 - 05:38:20 EDT
Dear collegues,
I wish to synthesize cis 2,4-dobromo-3-
hydroxy methylbutanoate supposedly by adding a
Halohydrin(BrOH) to methyl 4-bromocrotonate,
(BrCH2CH=CH.COOCH3),using N-bromosuccinimide as the
bromine donor.Different solvents have been suggested.
-Which would be the ideal solvent of choice?
(Dimethyl sulfoxide-DMSO; acetone; water)?
In the two step mechanism of addition of the
Halohydrin
to unsymmetrical alkenes as postulated by Markownikoff
rule, the electrophile attacks so as to produce the
carbonium ion of greater stability.Just to clear a
doubt, in this case which would be the greater
product:
1) BrCH2.CHOH.CHBr.COOCH3
2) BrCH2.CHBr.CHOH.COOCH3
-Will the resulting product be a cocktail mixture of
cis/trans,l&d , meso isomers?
(This product is similar to
Ethyl-4-cyano-3-hydroxybutanoate,C7H11NO3,CAS#
141942-85-0, used to
make Atorvastatin,a synthetic lipid lowering agent).
jaininder2002$##$yahoo.com
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