Hydrochloric Acid → (4'-Butoxy[1,1'-biphenyl]-4-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-4′-n-butyloxybiphenyl (3.05 g) in tetrahydrofuran (60 ml) was added 1.55 M n-butyllithium in n-hexane (7.74 ml) at −60° C. over a period of 10 minutes. The solution was stirred at −30° C. for 1.5 hours and cooled to −60° C. To the solution was added triisopropylborate (3.46 ml) over a period of 5 minutes, and the mixture was stirred for 1.5 hours without cooling. To the solution was added 1N hydrochloric acid (20 ml) and the solution was stirred for 30 minutes and extracted with ethyl acetate. The organic layer was separated and washed with water, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with n-hexane. The solid was collected by filtration and dried under reduced pressure to give 4-(4-n-Butyloxyphenyl)phenylboronic acid (2.31 g).

Provenance & Evidence