Sulfuric Acid → Methyl 5-bromoisoquinoline-4-carboxylate

Participants

Reaction Steps

To a mixture of conc. H2SO4 (16 mL) and methyl isoquinoline-4-carboxylate (Intermediate-15) (2.8 g, 15 mmol) at 0° C. was added, NBS (3.3 g, 18.7 mmol) slowly and the reaction mixture was allowed to come to RT and stirred overnight. After completion (TLC), it was quenched with ice, neutralized (NaHCO3) and extracted with EtOAc (50 mL×3). The organic phase was separated, dried (Na2SO4) and concentrated to give dark brown oil (3.6 g) as crude product that was purified by flash column chromatography (25% EtOAc in Hexanes) to furnish the desired compound (1.4 g, 35%).

Provenance & Evidence