[pinkman]

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.

[chenbeier]

Benzoic acid => nitration=> Dinitro benzoic acid  => Reduction => Diamino benzoic acid => Diazote and Sandmeyer with CuBr. => Di bromo Bromo acid
Ester can be made probably between.

[rolnor]

You can buy this;

https://www.sigmaaldrich.com/catalog/search?term=3%2C5-Dibromobenzoic+acid&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=SE&focus=productN=0%20220003048%20219853286%20219853235

[pinkman]

Benzoic acid => nitration=> Dinitro benzoic acid  => Reduction => Diamino benzoic acid => Diazote and Sandmeyer with CuBr. => Di bromo Bromo acid
Ester can be made probably between.

Thank you, this is very helpful! I would appreciate it if anyone could recommend specific articles that include simple experimental procedures for these steps.

[AWK]

Check Experimental Organic Chemistry Textbooks, also 96 volumes of Organic Syntheses

[pinkman]

Check Experimental Organic Chemistry Textbooks, also 96 volumes of Organic Syntheses

Ok thank you.

[wildfyr]

5g/85$ from Sigma isn't half bad...