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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: pinkman on January 13, 2020, 02:09:06 PM

Title: Bromination
Post by: pinkman on January 13, 2020, 02:09:06 PM

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.

Title: Re: Bromination
Post by: chenbeier on January 13, 2020, 04:19:07 PM

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.

Title: Re: Bromination
Post by: rolnor on January 13, 2020, 04:42:11 PM

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

Title: Re: Bromination
Post by: pinkman on January 13, 2020, 05:39:35 PM

Quote from: chenbeier on January 13, 2020, 04:19:07 PM

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.

Title: Re: Bromination
Post by: AWK on January 13, 2020, 05:51:25 PM

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

Title: Re: Bromination
Post by: pinkman on January 14, 2020, 09:27:20 AM

Quote from: AWK on January 13, 2020, 05:51:25 PM

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

Ok thank you.

Title: Re: Bromination
Post by: wildfyr on January 14, 2020, 11:26:41 AM

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