Trimethyl borate → [4-(Tert-butoxycarbonyl)-2,6-diethoxyphenyl]boronic acid

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Reaction Steps

To a stirred solution of tert-butyl 4-bromo-3,5-diethoxybenzoate (1 g) in THF (20 ml) was added n-BuLi (1.6M in hexane, 3.6 ml) at −78° C. under argon atmosphere and stirred at the same temperature for 1 h. To the mixture was added B(OMe)3 (777 ul) at −78° C. and the mixture was allowed to warm up to at room temperature. After stirring for further 1 h, the mixture was poured into ice-HCl aq., extracted with EtOAc, washed with brine and dried over sodium sulphate. After filtration and concentration, the residue was purified by silicagel column chromatography (hexane/EtOAc) to give the title product as a colorless solid.

Provenance & Evidence