56454-30-9Relevant academic research and scientific papers
Synthesis of 2- and 3-substituted N-methylpyrroles
Dvornikova, Elena,Kamieńska-Trela, Krystyna
, p. 1152 - 1154 (2007/10/03)
A reliable method of synthesis of 3-bromo-N-methylpyrrole by the use of N-bromosuccinimide and a catalytic amount of PBr3 is reported. The method described opens a facile route to a variety of 3-substituted pyrroles, which are otherwise difficult to access. In addition, conditions under which pure 2-bromo-N-methylpyrrole can be obtained have been established.
Bromination and Chlorination of Pyrrole and Some Reactive 1-Substituted Pyrroles
Gilow, H. M.,Burton, D. Edward
, p. 2221 - 2225 (2007/10/02)
Monobromination of pyrrole and 1-methyl-, 1-benzyl-, and 1-phenylpyrrole with 1 mol of N-bromosuccinimide in tetrahydrofuran results in the regiospecific formation of the 2-bromopyrroles.A little disubstitution is observed.Similarly, brominations with 2, 3, or 4 mol of NBS form primarily the di-, tri-, and tetrabromopyrroles, respectively.The thermodynamically more stable 3-bromopyrroles are the major monobrominated products observed when bromine is used as the brominating agent due to isomerization of the 2-bromopyrroles with hydrogen bromide.These reaction mixtures are further complicated because of disproportionation reactions.Chlorination with N-chlorosuccinimide gave results similar to those for the bromination with NBS, but the reaction is not as selective.
