5-Bromo-2-iodopyrimidine

32779-36-5

183438-24-6

General procedure for the synthesis of 5-bromo-2-iodopyrimidine from 5-bromo-2-chloropyrimidine: 5-bromo-2-chloropyrimidine (5.80 g, 30 mmol) and sodium iodide (7.5 g, 50 mmol) were suspended in chloroform (20 mL), and hydriodic acid (57 wt%, 2.85 g, 25.6 mmol) was slowly added at 0 °C. After cooling was withdrawn, the reaction mixture was stirred at room temperature for 20 hours. Subsequently, the reaction mixture was poured into a mixture of 200 mL of ice water with 30 mL of 10 N sodium hydroxide solution. Chloroform (150 mL) was added and stirred for 10 minutes. The organic phase was separated and the aqueous layer was extracted with chloroform (2 x 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 5-bromo-2-iodopyrimidine as a light yellow solid. Yield: 6.29 g (84%). Mass spectrum (MS): M = 284.8 (ESI+). 1H-NMR (300 MHz, CDCl3): δ 8.54 (s, 2H), 7.56 (d, J = 16.4 Hz, 1H), 7.59-7.66 (m, 4H).