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jmister28
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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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What are you resources? 2-bromobenzoic acid?
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Loptr
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Sure. What do you have?
SOCl2 + 2-bromobenzoic acid
You have SOCl2, right?
"Question everything generally thought to be obvious." - Dieter Rams
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jmister28
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yes I have SOCL2 Thanks
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jmister28
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how do I preform the reaction, reflux?
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jmister28
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As I am a beginner I am not sure
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walruslover69
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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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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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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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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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Have you typed it into scifinder (if you have university access)?
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jmister28
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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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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
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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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| 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
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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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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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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]
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clearly_not_atara
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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.
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jmister28
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does anyone have a good procedure for the sugasawa reaction?
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jmister28
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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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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]
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hacker
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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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CuReUS
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| 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 ? Good find atara.I was also thinking of using nitrile but more in the lines of a hoesch reaction.
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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2-Amino-2’-bromo-5-chlorobenzophenone is the target molecule
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Loptr
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| 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
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Where are you getting this ZnCl3 from? I am not familiar with that one....
(doesn't exist outside of solution, IIRC)
"Question everything generally thought to be obvious." - Dieter Rams
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jmister28
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sorry, typo ZnCl2
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