June 25, 2024, 01:34:29 PM
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Topic: Bromination  (Read 2319 times)

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Offline mujic

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Bromination
« on: May 14, 2024, 07:12:28 AM »
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 Hunter2

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Re: Bromination
« Reply #1 on: May 14, 2024, 07:27:57 AM »
Benzoic acid to Di- Nitro Benzoic acid, reduce to Diaminobenzoic acid(ester), then Diazoting and Sandmeyer to Bromo Compound.

Offline rolnor

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Re: Bromination
« Reply #2 on: May 15, 2024, 01:44:49 AM »

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

Offline Hunter2

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Re: Bromination
« Reply #3 on: May 15, 2024, 02:59:28 AM »
Better FeBr3 as catalyst in this case. Risk to get also Chloro Derivate if FeCl3 is used.

Offline rolnor

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Re: Bromination
« Reply #4 on: May 15, 2024, 02:09:49 PM »
That's true, thanx. It's possible no catalyst is required

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