Hydrochloric Acid → (4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid

Temperature

-78 °C

To a solution (100 mL) of 5-(benzyloxy)-2-bromo-1,3-dimethylbenzene (8.78 g, 30.2 mmol) in tetrahydrofuran was added n-butyllithium hexane solution (1.6 M, 22.6 mL, 36.2 mmol) under stirring at −78° C. The reaction mixture was stirred at the same temperature for 1.5 hr, and triisopropyl borate (20.9 mL, 90.6 mmol) was added. The mixture was allowed to warm to room temperature and stirred overnight. To the reaction mixture was added 2 M hydrochloric acid (150 mL) and the mixture was stirred for 2.5 hr. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. Cold hexane was added to the residue to allow crystallization. The precipitated crystals were collected by filtration, washed with cold hexane and dried to give the title compound (4.65 g, yield 60%) as colorless crystals.

1. stirringThe reaction mixture was stirred at the same temperature for 1.5 hr
2. temperatureto warm to room temperature
3. stirringstirred overnight
4. stirringthe mixture was stirred for 2.5 hr
5. customThe mixture was partitioned between ethyl acetate and water
6. washThe organic layer was washed with saturated brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. additionCold hexane was added to the residue
10. customcrystallization
11. filtrationThe precipitated crystals were collected by filtration
12. washwashed with cold hexane
13. customdried

ORD record

ord-596e2c1279d84347ba6fc2bfa9502de3

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2