Synthesis
Under nitrogen protection, sodium borohydride (3.1 g, 86 mmol) and titanium tetrachloride (1 M in toluene, 43 mL, 43 mmol) were dissolved in 40 mL of anhydrous 1,2-dimethoxyethane and the solution was cooled to 0 °C. Subsequently, 1-(2-bromophenyl)ethanone oxime (4.6 g, 21.5 mmol) was slowly added dropwise to the above cooled solution. After the dropwise addition was completed, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction was quenched with 200 mL of water and the mixture was adjusted to alkaline with ammonium hydroxide. The crude product was extracted with a solvent mixture of toluene and ethyl acetate to separate the organic and aqueous layers. The organic layer was dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure to give the crude product 1-(2-bromophenyl)ethylamine (4.0 g, 100% yield). Mass spectrum (electrospray ionization) m/z 200/202 [M + 1]+.
