Synthesis
General method: 3-nitrophenylboronic acid (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed. Subsequently, 2N aqueous hydrochloric acid solution was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3). The organic layer was extracted three times with saturated aqueous sodium bicarbonate solution and combined. The organic layer was subsequently washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure. Finally, the crude product was purified by silica gel column chromatography to afford the target compound 3-aminophenylboronic acid.
References
[1] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649
[2] Journal of the American Chemical Society, 1932, vol. 54, p. 4415,4418
[3] Journal of Organic Chemistry, 1937, vol. 2, p. 522,533
[4] Journal of the American Chemical Society, 1931, vol. 53, p. 713
[5] Patent: US2007/209123, 2007, A1. Location in patent: Page/Page column 7
