Potassium tert-butoxide → 6-Bromo-2-isopropenylquinoline

Participants

Reaction Steps

To a stirred suspension of (methyl)triphenylphosphonium bromide (2000 mg, 5.60 mmol) in dry THF (15 ml) was added a solution of potassium tert-butoxide (628 mg, 5.60 mmol) in dry THF (10 ml) with ice cooling. The mixture was then allowed to warm to room temperature. After 2 hours at room temperature, to this was added a solution of 1-(6-bromoquinolin-2-yl)ethanone (Step CA1B) (700 mg, 2.80 mmol) in dry THF (15 ml) with ice-cooling then the mixture was allowed to warm to room temperature. After 3 hours at ambient temperature, the mixture was quenched with water and extracted with ethyl acetate (×2). The combined solution was washed with brine, dried over sodium sulfate and concentrated in vacuo to give crude product, which was purified by column chromatography on silica gel (250 g) with hexane-ethyl acetate (10:1) to furnish the title compound (661 mg, 95%) as a tan solid. 1H NMR (270 MHz, CDCl3) δ 2.34 (3H, s), 5.50 (1H, s), 5.93 (1H, s), 7.65-7.78 (2H, m), 7.88-8.03 (3H, m). MS (ESI): m/z 248.11, 250.14 [M+H]+.

Provenance & Evidence