Sidmadra
Hazard to Others
Posts: 129
Registered: 17-2-2017
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What are some weak-chlorinating agents for chlorinating a phenolic compound?
I have a bi aryl compound, that I want to chlorinate ortho to one of the phenol groups on one ring. It's the only spot available that could react, and
the other ring doesn't have any activating constituents. My understanding is that phenols can undergo halogenation without a catalyst, but for
chlorination I am unsure which approach to take.
Hypochlorites are probably out of the question due to their strength in chlorinating even relatively unactivated rings. The next best thing that comes
to mind is an oxidation using H2O2/AcOh/Ammonium Salt, but I can only find references about that procedure using hydrobromide or iodide salts, so I'm
not sure if it would work for chlorination.
Is there something simple I am overlooking? I'm not used to working with phenolic compounds, and am I working on a very small scale (3-5 mmol) so I
prefer to use solids I can weigh for accuracy, if possible.
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Metacelsus
International Hazard
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Registered: 26-12-2012
Location: Boston, MA
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Sulfuryl chloride might work. See here: https://www.sciencedirect.com/science/article/pii/0040403995... and here: https://pubs.acs.org/doi/10.1021/jo402424h
Sadly, it's not a solid and it's not very amateur friendly. You could try N-chlorosuccinimide or trichloroisocyanuric acid, but I don't know how
selective those would be.
[Edited on 2019-4-1 by Metacelsus]
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