Dimethylformamide → N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Participants

Reaction Steps

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (500 mg, 2.28 mmol, 1 eq.) is dissolved in anhyd. DMF (5 mL) and cooled to 0° C. NaH (60% dispersion, 201 mg, 5.02 mmol, 2.2 eq.) is added and the resulting mixture is stirred at 0° C. for 30 min after which iodoethane (0.38 mL, 2.1 eq) is added dropwise to the reaction mixture. Once this addition is complete, the reaction mixture is allowed to warm to room temperature and stir for 3 days. The reaction is diluted with EtOAc and sequentially washed with H2O (5×) and saturated aqueous NaCl. The organic solution is dried over Na2SO4 and concentrated to give Diethyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine as a sticky tan solid: ESMS m/z 276.1 (M+H+).

Provenance & Evidence