N-bromobutanimide → 2-Bromo-1-(quinolin-8-yl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)quinoline (300 mg, 1.045 mmol) in THF (5 mL) and water (1 mL) was added NBS (203 mg, 1.149 mmol), and the resulting mixture was stirred at 25° C. for 30 min. The mixture was diluted with water (5 mL) and extracted in to EtOAc (2×5 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield crude 2-bromo-1-(quinolin-8-yl)ethanone (200 mg) (used without further purification in subsequent transformations): 1H NMR (400 MHz, DMSO-d6) δ 8.99-8.98 (1H, m), 8.27-8.23 (1H, m), 8.17-8.15 (1H, m), 7.67-7.63 (1H, m), 5.18 (1H, s), 5.02 (1H, s), 2.78 (2H, s). m/z (ESI, +ve) 249.9 (M+H)+.

Provenance & Evidence