31938-07-5

58971-11-2

General procedure for the synthesis of 3-bromophenethylamine from 3-bromocyanobenzyl: An anhydrous THF (100 mL) suspension of LiAlH4 (3.04 g, 80 mmol) was cooled to -5°C. Concentrated H2SO4 (3.9 g, 40 mmol) was added slowly dropwise and the resulting mixture was stirred for 1 h at -5°C. The reaction system was then brought to room temperature. Subsequently, a THF (5 mL) solution of 3-bromobenzeneacetonitrile (9.80 g, 50 mmol) was added slowly dropwise, and the reaction system was slowly warmed to room temperature after the dropwise addition. The reaction was continued to be stirred for 1 h at room temperature, then cooled to 0 °C and the reaction was quenched by addition of a 1:1 THF:H2O mixture (12.4 mL). Et2O (50 mL) was added, followed by 3.6 M NaOH solution (24.4 mL). The mixture was filtered through diatomaceous earth and the solids were washed well with additional Et2O. The organic phases were combined, dried over Na2SO4, filtered and concentrated in vacuum to give 3-bromophenethylamine (9.7 g, 97% yield). The crude product was used directly in the subsequent reaction.1H NMR (400 MHz, CDCl3) δ 7.38-7.30 (m, 2H), 7.20-7.10 (m, 2H), 2.96 (t, J = 7.2 Hz, 2H), 2.72 (t, J = 7.2 Hz, 2H), 1.35 (br s, 2H). m/z MS (ESI): calculated value: 199; measured value: 200/202 (M+-).