The problem would be how to protect the aromatic ring and also to stop the reaction after one bromine is substituted. Normally it goes through until tribromine derivate.
The problem would be how to protect the aromatic ring and also to stop the reaction after one bromine is substituted. Normally it goes through until tribromine derivate.
This looks as though this should be known chemistry, known conditions, yields, isolation, etc. Why wouldn't you just follow a lit procedure.
I always heard two opposite sayings, five minutes in the library can save five days in the lab, and of course, five minutes in the lab can save five days in the library (or something like that). Experience tells us which rule to follow.
This looks as though this should be known chemistry, known conditions, yields, isolation, etc. Why wouldn't you just follow a lit procedure.
I always heard two opposite sayings, five minutes in the library can save five days in the lab, and of course, five minutes in the lab can save five days in the library (or something like that). Experience tells us which rule to follow.
The methyl of the methyl ester won't be brominated. You can readily brominate the methyl group attached to the ring. You may see some ring bromination, but as Hunter2 asked, what conditions are you going to use?
The methyl of the methyl ester won't be brominated. You can readily brominate the methyl group attached to the ring. You may see some ring bromination, but as Hunter2 asked, what conditions are you going to use?
The problem would be how to protect the aromatic ring and also to stop the reaction after one bromine is substituted. Normally it goes through until tribromine derivate.
So how do you protect an aromatic ring? Did you mean the acidic group? To the OP, you can always make an ester, it adds a step but may be worth the time. Give the bromination of the free acid a try and see what happens.
The problem would be how to protect the aromatic ring and also to stop the reaction after one bromine is substituted. Normally it goes through until tribromine derivate.
So how do you protect an aromatic ring? Did you mean the acidic group? To the OP, you can always make an ester, it adds a step but may be worth the time. Give the bromination of the free acid a try and see what happens.
I dont think you can brominate the methyl of the methyl ester, or at least it will be unlikely, I think since it is next to an Oxygen which has two electron pairs the radical formed is too unstable (short lived) compared to radical on methyl which is stablized through resonance, I would imagine
I dont think you can brominate the methyl of the methyl ester, or at least it will be unlikely, I think since it is next to an Oxygen which has two electron pairs the radical formed is too unstable (short lived) compared to radical on methyl which is stablized through resonance, I would imagine
I don't think you'll need to protect the carboxylic acid. Radical bromination under the conditions you have given shouldn't mess with the acid, and I wouldn't worry about brominating the ring either. There are loads of examples in the literature in the presence of an unprotected acid (e.g. J Med Chem 2007, 5882).
You definitely shouldn't use Friedel-Crafts conditions, as this will certainly brominate the ring and wouldn't touch the methyl group.
I don't think you'll need to protect the carboxylic acid. Radical bromination under the conditions you have given shouldn't mess with the acid, and I wouldn't worry about brominating the ring either. There are loads of examples in the literature in the presence of an unprotected acid (e.g. J Med Chem 2007, 5882).
You definitely shouldn't use Friedel-Crafts conditions, as this will certainly brominate the ring and wouldn't touch the methyl group.
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Which is the method to do. add bromine and Aluminiumbromide? Or use light to get it in the methylgroup.
Which is the method to do. add bromine and Aluminiumbromide? Or use light to get it in the methylgroup.
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http://onlinelibrary.wiley.com/doi/10.1002/9780470638859.conrr680/abstract
http://onlinelibrary.wiley.com/doi/10.1002/9780470638859.conrr680/abstract
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I always heard two opposite sayings, five minutes in the library can save five days in the lab, and of course, five minutes in the lab can save five days in the library (or something like that). Experience tells us which rule to follow.
I always heard two opposite sayings, five minutes in the library can save five days in the lab, and of course, five minutes in the lab can save five days in the library (or something like that). Experience tells us which rule to follow.
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So how do you protect an aromatic ring? Did you mean the acidic group?
To the OP, you can always make an ester, it adds a step but may be worth the time. Give the bromination of the free acid a try and see what happens.
So how do you protect an aromatic ring? Did you mean the acidic group?
To the OP, you can always make an ester, it adds a step but may be worth the time. Give the bromination of the free acid a try and see what happens.
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You shouldn't plan to brominate the methyl position.
You should plan to find a catalog and buy some... it's not very expensive. If you want the ester, you can buy that too.
You shouldn't plan to brominate the methyl position.
You should plan to find a catalog and buy some... it's not very expensive. If you want the ester, you can buy that too.
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You definitely shouldn't use Friedel-Crafts conditions, as this will certainly brominate the ring and wouldn't touch the methyl group.
You definitely shouldn't use Friedel-Crafts conditions, as this will certainly brominate the ring and wouldn't touch the methyl group.
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