2-Fluoro-3-iodopyridine

Chemical Properties

Salmon-coloured solid

Uses

2-Fluoro-3-iodopyridine is typically used in scientific research and should not be used as a medicine, home remedy, or for other purposes.

Synthesis

General procedure for the synthesis of 2-fluoro-3-iodopyridine from 2-fluoropyridine: LDA (25.8 mL of a 2M THF solution, 51.5 mmol) was added slowly and dropwise to an anhydrous THF (50 mL) solution of 2-fluoropyridine (5.0 g, 51.5 mmol) at -78 °C. The reaction mixture was stirred continuously at -78 °C for 1 hour. Subsequently, a THF (30 mL) solution of I2 (13.07 g, 51.5 mmol) was added dropwise to the reaction system at the same temperature. After the reaction mixture continued to be stirred at -78 °C for 3 h, the reaction was quenched by the addition of H2O (10 mL) and slowly warmed to room temperature. Na2SO3 (50 mL, 2 M solution in water) was added to remove excess iodine. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and then concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography to afford 2-fluoro-3-iodopyridine (9.6 g, 83.6% yield) as a white solid. lC/MS analysis: m/z (M++H) = 224.

References

[1] Patent: EP1559320, 2005, A1. Location in patent: Page/Page column 6
[2] Journal of Organic Chemistry, 2002, vol. 67, # 10, p. 3487 - 3493
[3] Tetrahedron Letters, 2004, vol. 45, # 36, p. 6697 - 6701
[4] Patent: WO2013/6792, 2013, A1. Location in patent: Paragraph 0188
[5] Tetrahedron, 2004, vol. 60, # 29, p. 6113 - 6120