Background and overview of the preparation method of 6-hydroxynaphthalene-2-boronic acid
6-Hydroxynaphthalene-2-boronic acid is a pharmaceutical intermediate. Boric acid compounds are widely used in Suzuki cross-coupling reactions. Suzuki-Miyaura coupling reaction (SMC) is an important reaction to construct various C-C single bonds, and its main raw material is organic boronic acid compounds.
Preparation method of 6-hydroxynaphthalene-2-boronic acid to prepare hydrated terbium carbonate
Add 6-bromo-2-naphthol (2.23g, 10mmol) into the reaction bottle, add 40mL anhydrous tetrahydrofuran to dissolve, cool to -78°C, and add n-butyllithium (10ml, 25mmol) dropwise under nitrogen protection. , react with diphenylboric acid for 1 hour, add triisopropyl borate (2.82g, 15mmol) dropwise, react at low temperature for 0.5 hours, then rise to room temperature and continue to react for 0.5 hours. After TLC detection, after the reaction is completed, add 1M dilute hydrochloric acid to adjust the pH to Acidic, separate the organic phase, and extract the aqueous phase twice with diethyl ether. Combine the organic phases, wash with saturated brine, concentrate, and purify by column chromatography to obtain 1.13g of product with a yield of 60.2%.
References
[1] From PCT Int. Appl., 2017202207, 30 Nov 2017
