Nucleophilic aromatic substitution in the pyrrole ring: leaving group effect

A Annulli, P Mencareli, F Stegel

Index: Annulli, Alessandro; Mencarelli, Paolo; Stegel, Franco Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 4065 - 4067

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Citation Number: 10

Abstract

1-Methyl-2-nitropyrrolee was brominated with Br2 in AcOH, giving low yields of both 2- bromo-1-methyl-5-nitropyrrole (la, 3.7%) and 3-bromo-1-methyl-5-nitropyrrole (12.6%). This bromination procedure was not very reproducible: in some experiments we obtained only polybromo derivatives or 3-bromo-l-methylmaleimide. At-tempted brominations with Br2 in CF3COOH or CCl, were unsuccessful. A mixture of the two bromonitro derivatives was ...