Benzohydroxamic acid → N-((4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzamide

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Reaktionsschritte

N-hydroxybenzamide (0.17 g, 1.2 mmol) was dissolved in 8 mL of MeOH followed by the addition of 4-bromomethylphenyl boronic acid pinacol ester (0.40 g, 1.30 mmol). A 40% aqueous solution of NaOH (2 mL) was then added dropwise and the reaction was left to stir at reflux overnight. After cooling to room temperature and concentrated, concentrated HCl was added until a pH of 1 was observed. The resulting solution was then extracted with EtOAc and washed with brine. The organic layer was collected and dried over MgSO4 then purified via silica gel chromatography affording B16 in 6% yield (0.03 g, 0.07 mmol). 1HNMR (400 MHz, CDCl3) δ=8.61 (br, 1H, NH), 7.83 (d, J=8 Hz, 2H), 7.64 (d, J=7.6 Hz, 2H), 7.51-7.37 (m, 5H), 5.04 (s, 2H), 1.35 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=166.67, 138.45, 135.32, 132.35, 132.10, 128.95, 128.72, 127.25, 84.18, 78.45, 25.10. ESI-MS(+): m/z 354.10 [M+H]+, 376.10 [M+Na]+.

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