Reaktion #1778707

Reaktionsgleichung

triisopropyl borate

4-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-thiopyran

hexane

n-butyllithium

hydrochloric acid

→

title compound

Ausbeute 71.0%

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

Ausbeute 71.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred overnight
2. 2
   Temperaturcooled
3. 3
   workup.STIRRINGthe mixture was stirred for 2.5 hr
4. 4
   SonstigeThe mixture was separated into the aqueous layer
5. 5
   WaschenThe organic layer was washed with saturated brine and saturated aqueous sodium hydrogencarbonate
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   WaschenThe residue was washed with cold hexane

Vorschrift

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.

Quelle