Bromine → HCID 17863040, compound

Participants

Reaction Steps

To a solution (70 mL) of 1-(3-methylphenyl)-2-(4-pyrimidinyl)ethenol (3.0 g, 14 mmol) and sodium acetate (2.32 g, 28.26 mmol) in acetic acid was added dropwise a solution (70 mL) of bromine (0.72 mL, 14 mmol) in acetic acid at room temperature over 30 min. The mixture was stirred at room temperature for 2 hrs. Acetic acid was evaporated under reduced pressure, and aqueous sodium hydrogen carbonate solution was added to the residue. The mixture was extracted with ethyl acetate and the extract was dried and concentrated. The residue was dissolved in N,N-dimethylformamide (15 mL), and thiourea (1.1 g, 16 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 14 hrs. Aqueous sodium hydrogen carbonate solution was added, and the precipitated solids were collected by filtration. The solids were washed with water, dried and subjected to recrystallization from ethyl acetate to give the title compound (3.4 g, yield 89%).

Provenance & Evidence