Dibromomethane → 2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

関与物質

反応条件

反応手順

To a mixture of triisopropyl borate (20 g, 110 mmol), dibromomethane (8.6 ml, 120 mmol) and tetrahydrofuran (150 ml) was added dropwise n-butyllithium (2.6 M n-hexane solution, 39 ml, 100 mmol) at −78° C. (external temperature) over 1.5 hours. Then, the reaction mixture was stirred at the same temperature for 1.5 hours, and at room temperature for 2 hours. After the mixture was cooled at 0° C. (external temperature), to the reaction mixture was added methanesulfonic acid (6.5 ml, 100 mmol), and then, the reaction mixture was stirred at room temperature for 1 hour. After the mixture was cooled at 0° C. (external temperature), to the reaction mixture was added pinacol (12 g, 100 mmol), and then, the reaction mixture was stirred at room temperature for 1 hour. After the solvent was distilled off under reduced pressure, the resulting residue was distilled under reduced pressure (74-76° C., 8 mmHg) to obtain the title compound (16 g, 72 mmol, 68%).

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