8-Bromoquinoline → 8-Acetylquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromoquinoline (2.0 g, 9.661 mmol), tributyl(1-ethoxyvinyl)stannane (4.19 g, 11.59 mmol), and Pd(PPh3)4 (557 mg, 0.483 mmol) in toluene (50 mL) was heated under argon at 70° C. for 24 h. The mixture was cooled to RT and extracted with EtOAc (2×25 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 30% EtOAc/petroleum ether) furnished 1-(quinolin-8-yl)ethanone (1.2 g, 7.01 mmol, 73% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.99 (1H, dd, J=2 Hz & 2.4 Hz), 8.22 (1H, dd, J=2 Hz & 6.4 Hz), 7.95 (2H, d, J=7.6 Hz), 7.59 (1H, t, J=8 Hz), 7.48 (1H, dd, J=4 Hz), 2.95 (3H, s). m/z (ESI, +ve) 172.0 (M+H)+.

Provenance & Evidence