Hydrochloric Acid → (6-Phenylnaphthalen-2-yl)boronic acid

Temperature

60 °C

Under an argon gas atmosphere, a mixture of 100.0 g (353.1 mmol) of 2-bromo-6-phenylnaphthalene, 1.2 L of dehydrated THF and 1.2 L of dehydrated diethyl ether was cooled down to minus 20 degree C. Then, 280 ml (437 mmol) of hexane solution of 1.56M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 20 degrees for 1 hour. The reaction mixture was cooled down to minus 60 degrees C., and 199.3 g (1.06 mol) of triisopropylborate was dropped into the mixture. The reaction mixture was warmed up and then stirred at room temperature for 16 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. After the reaction, the reaction mixture was added with toluene, and aqueous phase thereof was eliminated. Then, organic phase thereof was washed with water and dried with magnesium sulfate, and the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid with hexane, 58.0 g of 6-phenylnaphthalene-2-boronic acid was obtained at an yield of 55%.

1. temperaturewas cooled down to minus 20 degree C
2. stirringThe reaction mixture was further stirred at minus 20 degrees for 1 hour
3. temperatureThe reaction mixture was warmed up
4. stirringstirred at room temperature for 16 hours
5. stirringstirred at room temperature for 1 hour
6. customAfter the reaction
7. washThen, organic phase thereof was washed with water
8. dry with materialdried with magnesium sulfate
9. distillationthe solvent was distilled away under reduced pressure
10. customBy recrystallizing the obtained solid with hexane

ORD record

ord-dcc8f95d67394404b9d055e0986e9b6a

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08568903B2