Hydrochloric Acid → 1,1'-Biphenyl-4-yl-boronic acid

Temperature

-95 °C

5 g of bromobiphenyl was dissolved in 100 mL of tetrahydrofuran(THF), and the solution was cooled to −95° C. Then, 20.2 mL of 1.6M butyllithium was added thereto and stirred for 5 minutes. 24.31 mL of trimethylborate was added thereto at −95° C., and the solution was stirred for 2 hours at −78° C., and for 12 hours at room temperature. Then, 10% HCl solution was added thereto at 0° C. to adjust the pH of the solution to be less than 6, and the solvent was distilled. The reaction product was extracted with ether to obtain biphenylboronic acid. Thereafter, as shown in the following reaction 4, 0.08 g of bromospiro-dimer, 0.034 g of biphenyl boric acid, 0.003 g of Pd(TPP)4 catalyst, 0.11 ml of 2M Na2CO3 were refluxed in 1,2-dimethoxyethane solvent while stirring for 24 hours (Suzuki coupling reaction) to obtain the target compound.

1. stirringat −95° C., and the solution was stirred for 2 hours at −78° C.
2. waitfor 12 hours at room temperature
3. customat 0° C.
4. distillationthe solvent was distilled
5. extractionThe reaction product was extracted with ether

ORD record

ord-e0f9b6fa3e8a4ccfb56e33a6f98ebe39

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326474B2