MD-P2P from crossed claisen condensation

[Grignard]

Could Etyl acetoacetate react with sodiumethoxide and
5-bromo-1,3-benzodioxole to yield MD-P2P under a standard crossed claisen condensation. Somebody tryed this? And P2P from bromobenzene under the same conditions??? And why not if thats the case, i remember i asked my highscool teacher of this some years ago, and she couldn`t answer me. She said the phenylgroup was to big and there maight be a steric hinder...

[Rhodium]

Alkylation of acetoacetate proceeds through an S_N2 mechanism, and if you review your organic chemistry literature, you'll discover that aromatic halides does not normally undergo any S_N2 reactions at all.

Your only hope here is to either form a benzyne intermediate (utfse/google) which can alkylate the acetoacetate anion or to instead use

use acetylacetone as your ketone

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/p2p.acetylacetonate.html)

[Grignard]

so it Wouldn`t work with cyanide group instead of Br either? thats to bad..

[Rhodium]

Cyanide sucks as a leaving group regardless of where it is attached. It will most certainly not abandon a phenyl ring just because an acetoacetate anion happened to sail by...

[silenziox]

Rhodium: aromatic halides does not normally undergo any SN2 reactions at all.

Not even if pushed to really extreme situations? I'm thinking about using ultrasound with external heating..

[Rhodium]

No, when a substitution of an aryl halide do occur, it is through another mechanism, such as benzyne formation, Nucleophilic Aromatic Substitution or metal-mediated oxidative addition/reductive elimination processes (usually involving Pd or Cu).

Google on the italicized terms for more information.