Hydrochloric Acid → (4-Phenylnaphthalen-1-yl)boronic acid

Temperature

-20 °C

Under an argon gas atmosphere, a mixture of 121.0 g (427.3 mmol) of 1-bromo-4-phenylnaphthalene, 1.2L of dehydrated THF and 1.2L of dehydrated diethylether was cooled down to −20 degrees C., and added with 360 ml (562 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for one hour at −20 degree C. The reaction mixture was further cooled down to −60 degrees C., and added with 241.1 g (1.28 mol) of triisopropyl borate in drops. The reaction mixture was subsequently warmed up to room temperature, and stirred for 16 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with toluene, so that aqueous phase thereof was eliminated. After organic phase thereof was cleansed with water and dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by hexane, 61.0 g of 4-phenylnaphthalene-1-boronic acid was obtained at an yield of 58%.

1. stirringThen, the reaction mixture was stirred for one hour at −20 degree C
2. temperatureThe reaction mixture was further cooled down to −60 degrees C
3. temperatureThe reaction mixture was subsequently warmed up to room temperature
4. stirringstirred for 16 hours at room temperature
5. stirringto be stirred for one hour at room temperature
6. customAfter the reaction
7. dry with materialdried with magnesium sulfate
8. distillationthe solvent was distilled away under reduced pressure
9. customBy recrystallizing the obtained solid by hexane

ORD record

ord-c100bfc907214f1a826be2f6e2c13c63

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08034256B2