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

Temperature

0 °C

To a mixture of triisopropyl borate (20 g, 110 mmol), dibromomethane (8.6 mL, 120 mmol), and tetrahydrofuran (150 mL) was added dropwise n-butyl lithium (2.6 M n-hexane solution, 39 mL, 100 mmol) over a period of 1.5 hours at −78° C., and then the reaction mixture was stirred for 1.5 hours at the same temperature. This mixture was then stirred for 2 hours at room temperature, after which it was cooled to 0° C., methanesulfonic acid (6.5 mL, 100 mmol) was added to the reaction mixture, and then the reaction mixture was stirred for 1 hour at room temperature. The mixture was cooled to 0° C., pinacol (12 g, 100 mmol) was added to the reaction mixture, and the reaction mixture was then stirred for 1 hour at room temperature. The reaction mixture was concentrated under a reduced pressure, after which the residue thus obtained was distilled under a reduced pressure (74-76° C., 8 mmHg) to obtain the title compound (16 g, 68%).

1. stirringThis mixture was then stirred for 2 hours at room temperature
2. stirringthe reaction mixture was stirred for 1 hour at room temperature
3. temperatureThe mixture was cooled to 0° C.
4. stirringthe reaction mixture was then stirred for 1 hour at room temperature
5. concentrationThe reaction mixture was concentrated under a reduced pressure
6. customafter which the residue thus obtained
7. distillationwas distilled under a reduced pressure (74-76° C., 8 mmHg)

ORD record

ord-66777c18e9f14f7ba638ae3747947439

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2