N-bromobutanimide → methyl 5-bromo-1-methyl-1H-pyrrole-3-carboxylate

Participants

Reaction Steps

A solution of methyl 1-methyl-1H-pyrrole-3-carboxylate (690 mg, 4.96 mmol) and NBS (883 mg, 4.96 mmol) in tetrahydrofuran (24.800 ml) was stirred at 25° C. for 1 h. The solution was then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (10-50% EtOAc in hexanes) affording methyl 5-bromo-1-methyl-1H-pyrrole-3-carboxylate (950 mg, 3.92 mmol, 79% yield) as an orange solid: LCMS (ES) m/e 218, 220 (M, M+2)+.

Provenance & Evidence