Pyridine → (R)-3-bromo-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one

Participants

Reaction Steps

To a solution of (R)-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one (0.1 g, example 223) in DMF (1 mL) were added pyridine (217 μL) and then bromine (12.6 μL) dropwise. The resulting solution was stirred at rt for 2.25 h. The reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted with 2× ethyl acetate. The organic layers were washed with water and once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by chromatography (SiO2, n-heptane/ethyl acetate 100:0 to 50:50) to give the title compound as a light brown solid (0.093 g; 78%), MS (ESI+): m/z=489.0 [M+H]+.

Provenance & Evidence