4,4'-Dibromobiphenyl → 4'-Bromo-4-biphenylboronic Acid (contains varying amounts of Anhydride)

Temperature

-80 °C

10.0 g (0.032 mol) of 4,4′-dibromobiphenyl was put in a 500 mL three neck flask, and nitrogen was substituted for air in the flask, and then 200 mL of tetrahydrofuran was added and stirred at −80° C. 20 mL (0.032 mol) of n-butyllithium (1.60 M hexane solution) was dropped into a reaction solution, and stirred for 1 hour at −80° C., and 40 mL (0.060 mol) of trimethyl borate was added and stirred for 1 hour while returning to room temperature. After 200 mL (1.0 mol/L) of hydrochloric acid water was added to the reaction solution, and stirred for about 12 hours, an organic layer was washed with a saturated sodium hydrogen carbonate solution and saturated saline, and then dried with magnesium sulfate. After the reaction solution was naturally filtered, a solid which was obtained by concentrating a filtrate, was recrystallized with a mixture of ethyl acetate and hexane. 3.7 g of 4-(4-bromophenyl)phenylboronic acid that was a target substance and was a white solid was obtained in a yield of 41% (Synthesis Scheme (e-1)).

1. stirringstirred for 1 hour at −80° C.
2. stirringstirred for 1 hour
3. customwhile returning to room temperature
4. stirringstirred for about 12 hours
5. washan organic layer was washed with a saturated sodium hydrogen carbonate solution and saturated saline
6. dry with materialdried with magnesium sulfate
7. filtrationAfter the reaction solution was naturally filtered
8. customa solid which was obtained
9. concentrationby concentrating a filtrate
10. customwas recrystallized with a mixture of ethyl acetate and hexane
11. customwas obtained in a yield of 41% (Synthesis Scheme (e-1))

ORD record

ord-4ff0515ca68e4dae99ebc31b11575e13

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686628B2