5-Bromo-2-iodopyrimidine → 5-bromo-2-ethenylpyrimidine

Participants

Reaction Steps

To a solution of 5-bromo-2-iodopyrimidine (14.2 g, 50 mmol) and Pd(PPh3)4 (865 mg, 0.75 mmol) in THF (200 mL) at room temperature under nitrogen was added dropwise vinylmagnesium bromide (100 mL, 100 mmol, 1 M in THF). The reaction mixture was heated to reflux for 2 hours. The formed mixture was quenched with water (200 mL) and extracted with EtOAc (200 mL×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford an oil which was purified by preparative column chromatography to afford 5-bromo-2-vinylpyrimidine (8 g, yield: 86%).

Provenance & Evidence