Uses
5-Bromo-2-fluoro-3-pyridylboronic acid is used in Suzuki cross-coupling reactions with aryl iodides in the presence of Pd(PPh3)4 and Na2CO3 to prepare 3-substituted 5-bromo-2-fluoropyridines[1].
Synthesis Reference(s)
The Journal of Organic Chemistry, 68, p. 3352, 2003
DOI: 10.1021/jo026864f
Synthesis
5-Bromo-2-fluoro-3-pyridylboronic acid is obtained by ortho-lithiation of 5-bromo-2-fluoropyridine with lithium diisopropylamide at −78 °C under nitrogen, followed by addition of trimethylborate, acidic workup to pH 6–7 with 2 M hydrochloric acid, and recrystallization from ethyl acetate and hexane in 80% yield[1].
References
[1]
Sutherland, A., Gallagher, T. (2003). Versatile Synthesis of 3,5-Disubstituted 2-Fluoropyridines and 2-Pyridones. The Journal of Organic Chemistry, 68(8), 3352–3355.
https://doi.org/10.1021/jo026864f
