N-bromobutanimide → (3-Bromomethyl-6-chloro-isoquinolin-5-yl)-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (6-Chloro-3-methyl-isoquinolin-5-yl)-acetic acid methyl ester (1.9 g, 7.63 mmol) in tetrachloromethane (190 mL) was added N-bromosuccinimide (1.36 g, 7.63 mmol). The reaction mixture was heated to 40° C. for 1 h under simultaneous irradiation by a 300 W UV lamp, filtered and the filtrate concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel, cyclohexane/EtOAc 80:20) to afford the title compound as a white powder (1.00 g, 3.05 mmol, 40%). MS (ES+): 328 (M(C13H1179Br35ClNO2)+H)+.

Provenance & Evidence