| Original language | English |
|---|---|
| Title of host publication | Encyclopedia of Reagents for Organic Synthesis (e-EROS, 2011) |
| Editors | Crich D., Charette A.B., Fuchs P.L., Rovis T. |
| Place of Publication | Online |
| Publisher | John Wiley & Sons Inc. |
| Pages | Online |
| Volume | 19 |
| Edition | 11 |
| ISBN (Print) | 9780470842898 |
| DOIs | |
| Publication status | Published - 2011 |
Abstract
(a bifunctional reagent that participates in SuzukiMiyaura cross-coupling and acylation reactions and serves as a precursor to the corresponding organotrifluoroborate) Alternate Names:5-formyl-2-furanboronic acid; 2-formylfuran-5-boronic acid; FFBA. Physical Data:orange-brown crystalline solid; variable melting points have been reported ranging from 142 to 150151°C.1-3 Solubility:soluble in aqueous n-butanol, aqueous ethanol, DMA, DME/ethanol, DMF, 1,4-dioxane, isopropanol, THF, and toluene. Analysis of Reagent Purity:by 1H and 13C NMR analysis,2, 3 by combustion analysis.3 The corresponding diethyl acetal can be analyzed for purity by reverse-phase HPLC.4 Preparative Methods:the compound can be prepared by metalating the diethyl or ethylene acetal of furfural with n-BuLi and then trapping the resulting aldehyde-protected (furan-2-yl)lithium with a trialkylborate followed by aqueous workup.1-3 Similarly, lithium N,O-dimethylhydroxylamide can also be similarly used to protect the aldehyde group in furfural.5 The compound is commercially available. Purification:by acid-promoted precipitation from aqueous solution2, 3 and/or by recrystallization from water.1, 2 Handling, Storage, and Precautions:the compound is corrosive and variable amounts of the corresponding anhydride can be formed during storage.