Dimethylamine → 3-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester

Participants

Reaction Steps

To a solution of 3-bromomethylphenyl boronic acid pinacol ester (Combi Block Inc., 297 mg, 1.0 mmol) in acetonitrile (5 mL) was added dimethylamine (2M solution in methanol, 2.0 mmol) followed by the addition of K2CO3 (691 mg, 5.0 mmol). The reaction mixture was stirred at room temperature for 16 h. Acetonitrile was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated NaHCO3, dried (MgSO4), filtered and the filtrate concentrated in vacuo to give dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine (INTERMEDIATE XI.1) as a viscous oil (200 mg, 0.77 mmol, 77%).

Provenance & Evidence