January 28, 2020, 04:30:04 AM
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Topic: Bromination  (Read 287 times)

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Offline pinkman

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Bromination
« 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.

Offline chenbeier

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Re: Bromination
« Reply #1 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.


Offline pinkman

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Re: Bromination
« Reply #3 on: January 13, 2020, 05:39:35 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.

Offline AWK

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Re: Bromination
« Reply #4 on: January 13, 2020, 05:51:25 PM »
Check Experimental Organic Chemistry Textbooks, also 96 volumes of Organic Syntheses
AWK

Offline pinkman

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Re: Bromination
« Reply #5 on: January 14, 2020, 09:27:20 AM »
Check Experimental Organic Chemistry Textbooks, also 96 volumes of Organic Syntheses

Ok thank you.

Offline wildfyr

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Re: Bromination
« Reply #6 on: January 14, 2020, 11:26:41 AM »
5g/85$ from Sigma isn't half bad...

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