Trimethyl borate → Dimethyl 2-(dimethylaminomethyl)benzeneboronate

Participants

Reaction Conditions

Reaction Steps

20.2 g (94.2 mmol) of the (2-bromobenzyl)dimethylamine prepared according to example 1 (2nd stage) were dissolved in 350 ml tetrahydrofuran and the solution was cooled to −70° C. in a cooling bath (isopropanol/dry ice). 68 ml (108 mmol) butyllithium solution (1.6 M in hexane) were added dropwise under nitrogen such that the temperature did not rise above −60° C. After the mixture had been stirred at −70° C. for two hours, 32 ml (282 mmol) trimethyl borate were also added dropwise such that the temperature did not rise above −60° C. The mixture was warmed to 25° C. in the course of 15 hours and the solution was concentrated on a rotary evaporator (500-10 mbar) without heat being supplied. The residue was taken up in 200 ml n-hexane, the mixture was stirred for one hour and filtered over an inert gas frit under nitrogen and the filtrate was concentrated on a rotary evaporator (500-10 mbar) without heat being supplied. 12.0 g dimethyl 2-(dimethylaminomethyl)benzeneboronate (61.5% of theory) were obtained in this manner.

Provenance & Evidence