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Author: Subject: synthesis of 2-bromobenzoyl chloride
jmister28
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[*] posted on 18-12-2018 at 15:30
synthesis of 2-bromobenzoyl chloride


Hi, I was wondering if any of you know a reaction to form 2-bromobenzoyl chloride because I can't seem to be able to find any resources for it. Any help is much appreciated.
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Tsjerk
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[*] posted on 18-12-2018 at 15:57


What are you resources? 2-bromobenzoic acid?
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Loptr
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[*] posted on 18-12-2018 at 16:00


Sure. What do you have?

SOCl2 + 2-bromobenzoic acid

You have SOCl2, right?




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jmister28
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[*] posted on 18-12-2018 at 16:03


yes I have SOCL2 Thanks
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jmister28
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[*] posted on 18-12-2018 at 16:08


how do I preform the reaction, reflux?
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jmister28
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[*] posted on 18-12-2018 at 16:15


As I am a beginner I am not sure
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walruslover69
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[*] posted on 18-12-2018 at 16:26


If you are a beginner, and don't know what you are doing, you should probably find a literature source for a similar reaction before working with something moderately dangerous like SOCL2. Whats the context for you making it?
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jmister28
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[*] posted on 18-12-2018 at 16:28


I am using the 2-bromobenzoyl chloride in a reaction with 4-chloroaniline with a ZnCl3 catalyst to produce 2-Amino-2’-bromo-5-chlorobenzophenone
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walruslover69
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[*] posted on 18-12-2018 at 16:49


What do you plan to do with the 2-Amino-2’-bromo-5-chlorobenzophenone? Seems like a series of complicated steps/reactions if you are just beginning to do amateur chemistry
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jmister28
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[*] posted on 18-12-2018 at 16:58


It is a synthetic pathway that I am trying to work out *Theoretically* to reach a new compound that uses the 2-Amino-2'-bromo-5-chlorobenzophenone

As I don't plan to carry the reaction in real life anytime soon I am just gathering the literature necessary for it
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walruslover69
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[*] posted on 18-12-2018 at 17:01


Have you typed it into scifinder (if you have university access)?
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jmister28
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[*] posted on 18-12-2018 at 17:10


no, I have not(I don't have university access) But I am using well known pathways and the only reagent that I needed to synthesize is the 2-bromobenzoyl chloride
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CuReUS
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[*] posted on 18-12-2018 at 17:55


Quote: Originally posted by jmister28  
I am using the 2-bromobenzoyl chloride in a reaction with 4-chloroaniline with a ZnCl3 catalyst to produce 2-Amino-2’-bromo-5-chlorobenzophenone
won't the acyl chloride just react with aniline rather than the ring ? ZnCl2 would also react with aniline
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UC235
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[*] posted on 18-12-2018 at 18:27


Quote: Originally posted by CuReUS  
Quote: Originally posted by jmister28  
I am using the 2-bromobenzoyl chloride in a reaction with 4-chloroaniline with a ZnCl3 catalyst to produce 2-Amino-2’-bromo-5-chlorobenzophenone
won't the acyl chloride just react with aniline rather than the ring ? ZnCl2 would also react with aniline


Yes. Also, it looks like OP is looking to make benzos, albeit poorly.
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jmister28
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[*] posted on 19-12-2018 at 09:01


If you were to react 4-chloroaniline, 2-bromobenzoyl chloride, and pyridine, take the product and react it with more 2-bromobenzoyl chloride and catalyze it with ZnCl2. would it not work to synthesize 2-Amino-2'-bromo-5-chlorobenzophenone.
Also, I am not trying to synthesize any benzodiazepines if I were, this would be a terrible method to do so.
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Metacelsus
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[*] posted on 19-12-2018 at 10:49


CuReUS is correct. You'll need a protecting group on the aniline, or else the amine will react with the acyl chloride.

It might be possible to acetylate the amino group, do the Friedel-Crafts acylation on the N-acetyl 4-chloroaniline, and then hydrolyze off the acetyl group.

[Edited on 2018-12-19 by Metacelsus]




As below, so above.
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clearly_not_atara
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[*] posted on 19-12-2018 at 11:12


I think it would be better to use 2-bromobenzonitrile and p-chloroaniline together in a Sugasawa reaction:

https://en.chem-station.com/reactions-2/2015/03/sugasawa-rea...

No protection and no acyl halide is required in this case.




[Edited on 04-20-1969 by clearly_not_atara]
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jmister28
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[*] posted on 19-12-2018 at 11:39


does anyone have a good procedure for the sugasawa reaction?
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jmister28
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[*] posted on 19-12-2018 at 11:57


what about this
https://www.researchgate.net/figure/Synthesis-of-2-amino-5-c...
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clearly_not_atara
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[*] posted on 19-12-2018 at 12:35


Haha, you're not trying to make benzos. You're interested in open-chain benzo analogs optimized for muscle relaxant activity. At least this is an interesting spoonfeed.

Do you have any plans for a skeletal muscle relaxant? Those kinds of things could be very dangerous in the wrong hands. The paper is here:

https://www.researchgate.net/publication/230795410_Synthesis...

You'll note that the FC acylation described in the diagram does not appear anywhere in the text of the paper; instead, they take the 2-aminobenzophenones as a starting point and add various groups to the nitrogen, of which o-tolyl (3e) seems to be the most successful.

As such, I think the acylation is provided only as a pictive example, and may not refer to a workable procedure. If I had to guess the ZnCl2 is actually catalyzing a Fries-type rearrangement, similar to this procedure:

http://anonym.to/https://www.tandfonline.com/doi/abs/10.1080...

[Edited on 19-12-2018 by clearly_not_atara]




[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 19-12-2018 at 22:28


You could start by brominating toluene with a Lewis acid catalyst, trichlorinate the methyl group under ultraviolet radiation. and then follow the procedure in US1557154 to hydrolyze to the target compound with water and a zinc chloride catalyst.
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[*] posted on 20-12-2018 at 05:07


Quote: Originally posted by Metacelsus  

It might be possible to acetylate the amino group, do the Friedel-Crafts acylation on the N-acetyl 4-chloroaniline, and then hydrolyze off the acetyl group.
wouldn't there be steric hindrance at the o-position ?
Quote: Originally posted by clearly_not_atara  
I think it would be better to use 2-bromobenzonitrile and p-chloroaniline together in a Sugasawa reaction
Good find atara.I was also thinking of using nitrile but more in the lines of a hoesch reaction.
Quote: Originally posted by clearly_not_atara  

As such, I think the acylation is provided only as a pictive example, and may not refer to a workable procedure.
My thoughts exactly.The lewis acid used would react with the NH2 of aniline -https://chemistry.stackexchange.com/questions/87145/why-does...
jmister,could you tell us for target molecule.Then maybe easier reactions or a better starting compound could be suggested :)
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jmister28
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[*] posted on 20-12-2018 at 06:47


2-Amino-2’-bromo-5-chlorobenzophenone is the target molecule
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[*] posted on 20-12-2018 at 13:58


Quote: Originally posted by jmister28  
I am using the 2-bromobenzoyl chloride in a reaction with 4-chloroaniline with a ZnCl3 catalyst to produce 2-Amino-2’-bromo-5-chlorobenzophenone


Where are you getting this ZnCl3 from? I am not familiar with that one....

(doesn't exist outside of solution, IIRC)




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jmister28
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[*] posted on 20-12-2018 at 18:31


sorry, typo ZnCl2
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