Reaction #1994261

Reaction equation

N-(biphenyl-4-yl)-N-(4-bromophenyl)biphenyl-4-amine

n-BuLi

2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)biphenyl-4-amine

Yield 33.0%

Solvents

THF

Conditions

Workup

1. 1
   Washthe resultant solution was sufficiently washed with distilled water and Brain
2. 2
   Otherpurified through column chromatography

Procedure

N-(biphenyl-4-yl)-N-(4-bromophenyl)biphenyl-4-amine (56 g, 0.117 mol) was introduced into a 2 L RBF, and dissolved in THF (600 ml). Then, the temperature was maintained at −78° C. for about 30 minutes. Then, n-BuLi (1.6M in Hex) (90 ml, 0.141 mol) was slowly added thereto. After 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (26.2 g, 0.141 mol) was added thereto, followed by heat-stirring at room temperature for 12 hours. After the reaction was completed, the resultant solution was sufficiently washed with distilled water and Brain, and purified through column chromatography to obtain N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)biphenyl-4-amine (white solid, 20 g, yield 33%).

Source