Tetrahydrofuran → Boronic Acid

Participants

Reaction Steps

Also, triphenylamine boronic acid product was synthesized as follows. Under an argon (Ar) atmosphere, 246 g of 4-bromotriphenylamine (commercially available product), and 1500 ml of anhydrous tetrahydrofuran were placed in a 5 liter flask, and 570 ml of 1.6M n-BuLi/hexane solution was added dropwise over 3 hours at −60° C. After 30 minutes, 429 g of triisopropyl borate was added dropwise over 1 hour. Then, reaction overnight at ambient temperature was allowed. After the reaction, 2 liters of water was added dropwise, and after that, the mixture was extracted and the liquid was separated using 2 liters of toluene. The organic layer was concentrated, recrystallized, filtered, dried and 160 g of white boronic acid product, a target compound, was obtained.

Provenance & Evidence