Hydrochloric Acid → Biphenyl-2-boronic acid

Temperature

-67 °C

Under an atmosphere of argon, 2-bromobiphenyl (20 g, 86 mmole) was dissolved into anhydrous ether (200 ml) and the resultant solution was cooled at −35° C. in a dry ice/methanol bath. To the cooled solution, a hexane solution of n-butyllithium (1.50 mole/liter, 63 ml, 95 mmole) was added dropwise and the resultant mixture was stirred at −20° C. for 1 hour. After the reaction mixture was cooled at −67° C., a solution (50 ml) of triisopropoxyborane (50 ml, 0.22 mole, 2.5 eq) in anhydrous ether was added and the resultant mixture was stirred at −65° C. for 1 hour and at the room temperature for 2 hours and left standing for one night. To the obtained reaction mixture, a 10% hydrochloric acid (200 ml) was added. After the resultant mixture was stirred at the room temperature for 1 hour, the formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried with anhydrous magnesium sulfate. The solid obtained after removing the solvent by distillation was washed with hexane and a white solid (11 g, 62%) was obtained.

1. waitleft
2. waitstanding for one night
3. customTo the obtained reaction mixture
4. customthe formed organic layer was separated
5. washwashed with a saturated aqueous solution of sodium chloride (50 ml)
6. dry with materialdried with anhydrous magnesium sulfate
7. customThe solid obtained
8. customafter removing the solvent
9. distillationby distillation
10. washwas washed with hexane

ORD record

ord-43a0359d51b243ab9785db2b415fb842

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361796B2