Hydrochloric Acid → [2,6-dimethyl-4-(tetrahydro-2H-thiopyran-4-yloxy)phenyl]boronic acid

To a solution of 4-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-thiopyran (3.01 g, 10.0 mmol) in tetrahydrofuran (50 mL) was added dropwise a hexane solution (1.6 M, 6.57 mL, 10.5 mmol) of n-butyllithium at −78° C. The reaction mixture was stirred at the same temperature for 1.5 hr, and triisopropyl borate (6.92 mL, 30.0 mmol) was added. After warming to room temperature, the mixture was stirred overnight. The reaction mixture was ice-cooled, 2 M hydrochloric acid (50 mL) was added, and the mixture was stirred for 2.5 hr. The mixture was separated into the aqueous layer and the organic layer. The organic layer was washed with saturated brine and saturated aqueous sodium hydrogencarbonate while adjusting to neutral, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with cold hexane to give the title compound (1.89 g, yield 71%) as colorless crystals.

1. stirringthe mixture was stirred overnight
2. temperaturecooled
3. stirringthe mixture was stirred for 2.5 hr
4. customThe mixture was separated into the aqueous layer
5. washThe organic layer was washed with saturated brine and saturated aqueous sodium hydrogencarbonate
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. washThe residue was washed with cold hexane

ORD record

ord-4d9df7d9c2a14527a2d5c72c6d3f0f30

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153694B2