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Topic: Reduce a ketone without removing a halogen?  (Read 3462 times)

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Offline mstout

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Reduce a ketone without removing a halogen?
« on: March 17, 2011, 04:19:44 AM »
I'm working on a synthesis and stopped at 3-bromo acetophenone. Is it possible to reduce the ketone without affecting the bromine? Clemmensen's or H2/Pd maybe?

My notes from class and book do not show a reduction method being performed on a molecule containing a halogen.

Thank you.

Offline discodermolide

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Re: Reduce a ketone without removing a halogen?
« Reply #1 on: March 17, 2011, 06:51:28 AM »
I'm working on a synthesis and stopped at 3-bromo acetophenone. Is it possible to reduce the ketone without affecting the bromine? Clemmensen's or H2/Pd maybe?

My notes from class and book do not show a reduction method being performed on a molecule containing a halogen.

Thank you.
Red-Al, li/NaBH3 etc
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Offline nox

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Re: Reduce a ketone without removing a halogen?
« Reply #2 on: March 17, 2011, 11:48:30 PM »
By reduce do you mean reducing it to the alcohol or removal of the functionality completely?

Because there's plenty of ways to do the former, you could probably just hit it with NaBH4 and the reaction will go. If it's the latter, you could probably try a Wolff-Kishner reduction on such a simple substrate.

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