Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: mstout on March 17, 2011, 04:19:44 AM

Title: Reduce a ketone without removing a halogen?
Post by: mstout 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.

Title: Re: Reduce a ketone without removing a halogen?
Post by: discodermolide on March 17, 2011, 06:51:28 AM

Quote from: mstout 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.

Red-Al, li/NaBH3 etc

Title: Re: Reduce a ketone without removing a halogen?
Post by: nox 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.