Dimethyl Sulfide → N-benzyl-2-(2-bromophenyl)ethanamine

Participants

Reaction Steps

2-(2-Bromophenyl)-N-(phenylmethyl)acetamide was dissolved THF (0.2 M), followed by addition of BH3.DMS (3 eq), and the reaction was heated to reflux with stirring. After 2 hrs, the mixture was cooled to room temerature, and quenched with excess 10% HCl. The mixture was heated to reflux for 1 hr, and then cooled to room temperature. After washing with EtOAc, the aqueous phase was made alkaline with 10% sodium carbonate, and extracted with EtOAc. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with EtOAc to afford a colorless solid. EI-MS m/z 290/292 (M+H)+

Provenance & Evidence