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how to synthesize 4-bromoresorcinol using resorcin?
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Topic: how to synthesize 4-bromoresorcinol using resorcin? (Read 6071 times)
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how to synthesize 4-bromoresorcinol using resorcin?
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on:
November 29, 2006, 06:24:03 AM »
I know how to make 4-bromoresorcinol using 2,4-dihydroxybenzoic acid, but now want to make it using resorcin, please help me.
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Last Edit: November 29, 2006, 06:29:52 AM by plain
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Custos
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Re: how to synthesize 4-bromoresorcinol using resorcin?
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Reply #1 on:
November 29, 2006, 07:33:28 PM »
The direct bromination of resorcinol can be carried out using bromine in methanol (for example) but you will end up with a mixture of monobromoresorcinol (both 2 and 4) and di-bromoresorcinols... all difficult to separate. The Organic Synthesis prep of 4-bromoresorcinol (
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0100
) goes through the benzoic acid. Or of course you could just buy 4-bromoresourcinol from Aldrich.
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tbuihuu
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Re: how to synthesize 4-bromoresorcinol using resorcin?
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Reply #2 on:
November 29, 2006, 07:56:46 PM »
resorcinol reacts with Br
2
/Fe --->4-bromresorciol (major)
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maurice
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Re: how to synthesize 4-bromoresorcinol using resorcin?
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Reply #3 on:
November 29, 2006, 09:21:44 PM »
NBS or Br2/H2O2
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plain
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Re: how to synthesize 4-bromoresorcinol using resorcin?
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Reply #4 on:
November 30, 2006, 03:12:12 AM »
I want to synthesize 1 kg 4-bromoresorcinol and what mean is the best choise for me to do it. Of course, the cost is as lower as possible and the process is simple. Thanks.
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Custos
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Re: how to synthesize 4-bromoresorcinol using resorcin?
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Reply #5 on:
November 30, 2006, 06:57:42 PM »
For large scale work I would stick to the Organic Synthesis prep. They are usually very robust as they have been tested, usually at reasonable scale. Make the dihydroxybenzoic acid from resorcinol using this prep:
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0557
then brominate and decarboxylate using this prep:
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0100
I seriously think that if you try a direct bromination you will end up with a mess of positional isomers and overbrominated products that will be difficult to purify.
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