Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: democanarchis on May 13, 2010, 03:42:55 PM
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I'm having a bit of a headache trying to separate two compounds. One is the product from a sandmeyer reaction, a 1-bromo-2-chloronaphthalene. The second is the 1-bromonaphthalene which is generated in a side reaction. The compound can only be purified by running a column in neat heptane, and I have no access to reverse phase or prep hplc. I have about 600mg of the products in a 3:1 ratio.
The compounds co-elute on every mobile phase i've tried. The main 1,2 halogenated product has a MP of 46 and the minor a MP of 6 degrees C, but as a mixture are an oil. Their respective boiling points are too close to do a short path distillation, and there isn't enough material to do a conventional distillation.
Any suggestions?
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Do you have access to a prep gc?
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If you're using the Sandmeyer reaction to substitute chlorine, why are there bromine side products?
Given that the main product has a melting point of 46 degrees, have you considered a recrystallistation?