Water → 2-phenyl-6-vinylquinolin-4(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-2-phenylquinolin-4(1H)-one 1 (1.5 g, 5.0 mmol) in DMSO (60 mL) was added vinyltributyl tin (1.75 mL, 6.0 mmol) and tetrakis-triphenylphosphine palladium (116 mg, 0.1 mmol). The mixture was then heated to 100° C. for 20 h, at which time, LC-MS revealed the disappearance of starting material. The reaction was then poured into a mixture of EtOAc (200 mL) and water (400 mL) which caused a grayish solid to precipitate. This solid was collected and dried under vacuum in a desiccator over night to yield 1.21 g (97% yield) of 2-phenyl-6-vinylquinolin-4(1H)-one which was pure by 1H NMR and LC-MS. 1H NMR (400 MHz, DMSO-d6) ppm: 11.75 (br s, 1H), 8.08 (s, 1H), 7.85 (m, 3H), 7.74 (d, J=8.8 Hz, 1H), 7.59 (m, 3H), 6.88 (dd, J=17.6 Hz, 10.8 Hz, 1H), 6.34 (s, 1H), 5.90 (d, J=17.6 Hz, 1H), 5.30 (d, J=10.8 Hz, 1H). LRMS (CI, [M+H]) Calc'd=248.2. found=248.2. HRMS (APCI, [M+H]+) Calc'd for C15H11BrNO: 248.1070. found: 248.1068.

Provenance & Evidence