858271-08-6

Upstream product

• 2436-79-5 diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate 
• 2199-51-1 2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 98-88-4 benzoyl chloride 

Downstream Products

• 73652-62-7 1-benzoyl-5-chloro-2-chloromethyl-3-ethoxycarbonyl-4-methylpyrrole 
• 73652-61-6 1-benzoyl-5-bromo-3-ethoxycarbonyl-2,4-dimethylpyrrole 
• 73652-59-2 1-benzoyl-5-chloro-3-ethoxycarbonyl-2,4-dimethylpyrrole 

Relevant academic research and scientific papers

Direct oxidative coupling of: N -acyl pyrroles with alkenes by ruthenium(ii)-catalyzed regioselective C2-alkenylation

Ruthenium(ii)-catalyzed oxidative coupling by C2-alkenylation of N-acyl pyrroles with alkenes has been described. The acyl unit was found to be an effective chelating group for the activation of aryl C-H bonds ortho to the directing group. The alkenylation reaction of benzoyl pyrroles occurred regioselectively at the C2-position of the pyrrole ring, without touching the benzene ring. The reaction provides exclusively monosubstituted pyrroles under the optimized conditions. Disubstituted pyrroles could be obtained using higher loadings of the ruthenium(ii)-catalyst and the additives.

Electrophilic Heteroaromatic Substitutions. 2. Mechanism of the Side-Chain Halogenation of Polysubstituted α-Methylpyrroles with Molecular Chlorine

The mechanism of the α-side-chain chlorination with molecular chlorine in dichloromethane or chloroform solution at low temperatures and in the dark of polysubstituted α-methylpyrroles 1-4 has been investigated with regard to the nature of the reagent and to the fate of the attacking as well as the substituent halogen in the reaction products.Careful product analysis was carried out by radiochemical measurements (chlorine exchange), NMR spectra, standard halide ion titration, and preparative layer chromatography (PLC) techniques.The results suggest that the overall process consists of two main steps, i.e., the electrophilic nuclear attack and the subsequent rearrangement of the halogen to the side chain.Halogen migration from nucleus to side chain may occur from either the adjacent β or the vinylogous α' position.The present data provide a considerable extension of the concept of nonconventional electrophilic halogenation of aromatic molecules into the field of pyrroles.