Aromatic Synthesis problem, help.

[Handinhand]

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So how would you carry out this synthesis? It's got me stumped, since you can't do a friedel-crafts acylation on aniline, because the lone pair on N will form a complex with the lewis acid catalyst. Anybody know any other way to form C-C bonds on aromatic rings WITHOUT using an acid catalyst?

 

[loveoforganic]

You have to protect the nitrogen by reacting it with acetyl chloride.

By the way, this forum isn't for homework questions.

chemicalforums.com is a very good site for that.

 

[tresbon]

I thought aromatic compounds have been removed from the MCAT, or have they?

 

[Handinhand]

Oh it's not homework, just a problem I ran across and I figured here out of anywhere else on the forum would be the place to ask it.