Hydrochloric Acid → [3-(Naphthalen-1-yl)phenyl]boronic acid

Temperature

-60 °C

Under an argon gas atmosphere, a mixture of 200.0 g (706.3 mmol) of 1(3-bromophenyl)naphthalene and 2.1 L of dehydrated THF was cooled down to −60 degrees C., and added with 543 ml (847 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at −60 degree C. 398.5 g (2.119 mol) of triisopropyl borate was dropped into the reaction solution at −60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 17 hours. 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 dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 3-(1-naphthyl)phenylboronic acid was obtained at an yield of 67%.

1. stirringThen, the reaction mixture was stirred for two hours at −60 degree C
2. temperatureSubsequently, the reaction mixture was warmed up to room temperature
3. stirringstirred for 17 hours
4. stirringto be stirred for one hour at room temperature
5. customAfter the reaction
6. dry with materialAfter organic phase thereof was dried with magnesium sulfate
7. distillationthe solvent was distilled away under reduced pressure
8. customBy recrystallizing the obtained solid by toluene

ORD record

ord-0f238e604f6e41a081bb9798db468472

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08021574B2