Hydrogen Peroxide → 2,6-Dichloropyridin-3-ol

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Reaction Steps

H2O2 (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6-dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH2Cl2 (30 mL) at 0° C. After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na2S2O3 aqueous (50 mL) and adjusted to pH<7 with 1N HCl. The mixture was extracted with EtOAc (40 mL×3). The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and the solvent was concentrated in vacuo to provide 2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4%). 1H-NMR (CDCl3, 400 MHz) δ 7.30 (d, J=8.4 Hz, 1H), 7.19 (d, J=8.4 Hz, 1H), 5.70 (br, 1H). MS (M+H)+: 164/166/168.

Provenance & Evidence