I am trying to synthesize a tetrakis (bromomethyl) anthracene derivative (as shown in the attached fig.). I am not able to brominate all the four methyl groups using NBS (4, 6 and 8 eq) in CCl4, Chloroform, DCM and EDC.
Could you please suggest the ways to get the product that I need.
Have you already tried to substitute NBS for elemental bromine? Probably you are going to loose some selectivity and will have to separate the isomers - I would give it a try though.
Good luck,
JME
Use a large excess of NBS and be sure to turn the lights on. This is a radical initiated process and CCl4 is the preferred solvent. Slow addition of AIBN over the course of the reaction may help as a thermal initiator with relatively innocuous side products, this has the potential of increasing radical concentrations. Use of a mercury or UV lamp is also recommended for much the same reason.
An alternative strategy (if the molecule is stable enough) would be to add a small quantity of trifluoroacetic acid. Protonation of NBS should decrease the photodissociation energy, however it also makes NBS more electrophilic and introduces acidity which may be at odds with your functional groups.
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