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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: malviyangr on April 14, 2011, 03:05:57 AM

Title: sodium salt of acetylacetone + bromomesitylene
Post by: malviyangr on April 14, 2011, 03:05:57 AM

Hi,
I am working on a reaction of a sodium salt of acetylacetone and 2,4,6-trimethylenebromo mesitylene in the presence of potassium iodide in ether. I took sodium salt in ether and added bromo compound in ether dropwise into it. And kept on stirring at room temperature. I want to ask, am i going in the right direction? Or what about the Chloroform as the solvent?
help me!!!!!!!!!please....

Title: Re: sodium salt of acetylacetone + bromomesitylene
Post by: Vidya on April 14, 2011, 08:18:37 AM

Hi
Sodium salt will be insoluble in ether

Title: Re: sodium salt of acetylacetone + bromomesitylene
Post by: malviyangr on April 16, 2011, 02:28:32 AM

yes, i know...sodium salt will be insoluble in ether...but according to my knowledge.. sodium salt will be soluble on addition of bromo compound dropwise....or should i use some other solvent????thanks for any suggestion..

Title: Re: sodium salt of acetylacetone + bromomesitylene
Post by: orgopete on April 22, 2011, 06:41:48 PM

As written, that won't react. You cannot displace an unactivated aryl bromide with an enolate. If the one of the methyl groups were a nitro, then it could go by addition-elimination.

Title: Re: sodium salt of acetylacetone + bromomesitylene
Post by: Kadabrium on April 23, 2011, 06:23:38 AM

hi that's not aryl bromide but sth like BrCH2Ar..
 i think they can react just in water..

Title: Re: sodium salt of acetylacetone + bromomesitylene
Post by: orgopete on April 23, 2011, 06:45:00 AM

Use an SN2 solvent. This looks pretty simple so I don't think you need to use DMSO or DMF, but I agree that ether is pushing it. I'd probably just use alcohol.