Water → 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Participants

Reaction Conditions

Reaction Steps

3.7 g (10 mmol) of (4-bromophenyl)naphthalen-1-yl-phenylamine was dissolved in 100 ml of THF and cooled to −78° C. 4.8 ml (12 mmol) of 2.5M n-butyllithium was added slowly to the THF solution and maintained at the same temperature as above for an hour to allow reaction. 2.2 g (12 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added to the reactant solution, maintained at the same temperature as above for an hour to allow reaction, heated to room temperature (RT) and stirred for 24 hours. Water was added to end the reaction, and 300 ml of chloroform was added. The resulting organic layer was washed with 200 ml of water and dried with anhydride magnesium sulfate. 3.4 g of Naphthalen-1-yl-phenyl[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylamine (intermediate A) was obtained through silica chromatography with a yield of 81%.

Provenance & Evidence