Triisopropyl borate → HCID 58288411, compound

Participants

Reaction Conditions

Reaction Steps

Under argon and at −78° C., 20.2 ml (50.42 mmol) of a 2.5 M solution of n-butyllithium in hexane were slowly added dropwise to a solution of 15 g (38.79 mmol) of N,N-dibenzyl-5-bromo-2-chloroaniline in 350 ml of THF/diethyl ether (1:1). The reaction solution was stirred at −78° C. for 60 min, and 14.3 ml (62.1 mmol) of triisopropyl borate were then added slowly. The reaction solution was subsequently stirred at −78° C. for another 15 min, then slowly warmed to room temperature, and stirring at this temperature was continued overnight. 150 ml of ice-water were then metered in. The organic phase was separated off, and the aqueous phase was then extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulphate. After filtration, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→4:1). This gave 9 g (66% of theory) of the title compound.

Provenance & Evidence