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Bromination

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mujic:
I want to synthesize methyl 3,5-dibromobenzoate (3,5-dibromobenzoic acid methyl ester).

This can be synthesized from the corresponding benzoic acid, ester, or aldehyde, which are all meta- directing. However, they strongly deactivate the benzene ring and make bromination difficult. Even if the first bromination is achievable, i cannot find any papers on how to do the second one.

I don't have access to an already bromo- substituted benzene compound.

Is there an easier synthetic route? I am struggling in finding any papers for reference.

I am very new to Organic Chemistry and although it seems like an easy target I still find it extremely difficult.

Hunter2:
Benzoic acid to Di- Nitro Benzoic acid, reduce to Diaminobenzoic acid(ester), then Diazoting and Sandmeyer to Bromo Compound.

rolnor:

I think its straightforward to di-brominate benzoic acid, the dibromo acid is available on many vendors. You might need FeCl3 as catalyst.

Hunter2:
Better FeBr3 as catalyst in this case. Risk to get also Chloro Derivate if FeCl3 is used.

rolnor:
That's true, thanx. It's possible no catalyst is required

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