2-Fluorophenylboronic Acid

Abstract

[1993-03-9] C6H6BFO2 (MW 139.92) InChI = 1S/C6H6BFO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H InChIKey = QCSLIRFWJPOENV-UHFFFAOYSA-N (a reagent and substrate that is used to prepare chiral nonracemic P,N-ligands and Lewis acids, it is also commonly employed in palladium-catalyzed Suzuki coupling reactions) Physical Data: mp 101–110 °C (contains varying amounts of the anhydride). Solubility: soluble in water (sparingly) and most organic solvents. Form Supplied in: white crystalline solid. Analysis of Reagent Purity: HPLC, IR, NMR. Preparative Methods: ortho-lithiation of fluorobenzene with sec-butyllithium in tetrahydrofuran at −78 °C, treatment with trimethyl borate (−78 °C to room temperature), and subsequent hydrolysis.1 2-Fluorophenylboronic acid can also be prepared from 1-bromo-2-fluorobenzene [transmetallation with n-butyllithium at −78 °C, treatment with trimethyl borate (2 equiv, −78 °C to room temperature), and subsequent hydrolysis with 1 M hydrochloric acid] in good yield (80%) on recrystallization from boiling water.2 Purification: recrystallization from ether or water.1, 2 Handling, Storage, and Precautions: the compound should be handled with protective gloves and eyewear in a ventilated area. The compound is stable but care should be taken to avoid contact with strong oxidizing agents. Decomposition products include carbon monoxide, carbon dioxide, boron oxides, and hydrogen fluoride.