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Author: Subject: Help with synthesis of 5-Bromo-2-naphthoic acid
cirice1
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sad.gif posted on 1-4-2020 at 11:20
Help with synthesis of 5-Bromo-2-naphthoic acid


Hello i an looking for a pathway to synthesize 5-Bromo-2-naphthoic acid. I did find a synthesis for 5-Amino-4-hydroxy-2-naphthoic acid (https://www.sciencedirect.com/science/article/pii/S004040390...) and I am looking for a way to remove the hydroxy group to get to 5-Amino-2-naphthoic acid . Does anyone have an idea of how irt could be done or if there might be an easier way?. Thank you

5-Amino-4-hydroxy-2-naphthoic acid .png - 4kB 5-Amino-2-naphthoic acid .png - 4kB
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draculic acid69
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[*] posted on 1-4-2020 at 11:46


What about iodine and red phosphorus.or hypophosphorus acid and iodine (quicker, cleaner,better yeild)
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cirice1
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[*] posted on 1-4-2020 at 11:58


Quote: Originally posted by draculic acid69  
What about iodine and red phosphorus.or hypophosphorus acid and iodine (quicker, cleaner,better yeild)

I wasn't sure if it would work because all i could find when searching was meth related , couldn't find anything about how it would interact with other groups
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Dr.Bob
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[*] posted on 1-4-2020 at 16:50


Not sure how to make the O-triflate without reacting the amine, but if you can do that, it is easily hydrogenated to the H. I think the diethylphosphate also can be hydrogenated, but not as sure.
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draculic acid69
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[*] posted on 1-4-2020 at 17:22


Quote: Originally posted by cirice1  
Quote: Originally posted by draculic acid69  
What about iodine and red phosphorus.or hypophosphorus acid and iodine (quicker, cleaner,better yeild)

I wasn't sure if it would work because all i could find when searching was meth related , couldn't find anything about how it would interact with other groups


Meth rxn has an amino group a hydroxyl a benzene ring.a lot of the same groups.so it's similar enough to look into doing the reduction the same.doesnt seem to be
any reason it won't work other than the alcohol is attached to the ring and that's like a phenol which can't be reduced easily but bcoz it's a napthyl ring not a phenol ring maybe what applies to phenol don't apply here so hopefully it's that simple.maybe not but worth looking into.

[Edited on 2-4-2020 by draculic acid69]
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