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2-Fluorophenylboronic Acid

Publication Date Apr 15, 2006

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.

Concepts

Trimethyl Borate Subsequent Hydrolysis Ventilated Area Protective Gloves Boron Oxides Hydrogen Fluoride Hydrochloric Acid Physical Data Lewis Acids Water Organic Solvents

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