Trimethyl borate → {4-[(Cyclobutyloxy)methyl]-2,6-dimethoxyphenyl}boronic acid

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Reaction Steps

To a mixture of 2-bromo-5-[(cyclobutyloxy)methyl]-1,3-dimethoxybenzene (2.39 g, 7.94 mmol) and THF (20 mL) was added n-butyllithium (2.73M n-hexane solution: 3.49 mL, 9.53 mmol) at −78° C. (internal temperature), and the mixture was stirred for one hour. To the mixture was added trimethyl borate (1.07 mL, 9.53 mmol) and the mixture was gradually warmed to room temperature while stirring. Thereafter, a saturated aqueous solution of ammonium chloride was added to the mixture while cooling on ice, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. To the residue, heptane (30 mL) was added, the precipitated solid was filtered and then dried under reduced pressure to obtain the title compound (905 mg, 3.40 mmol).

Provenance & Evidence