Sulfuric Acid → 3-Bromophenethylamine

Participants

Reaction Conditions

Reaction Steps

A suspension of LiAlH4 (3.04 g, 80 mmole) in dry THF (100 mL) was cooled to −5° C. Concentrated H2SO4 (3.9 g, 40 mmole) was added dropwise, and the resulting mixture was stirred at −5° C. for 1 hour. A solution of 3-bromo-benzenacetonitrile (9.80 g, 50 mmole) in THF (5 mL) was added dropwise, and the reaction was allowed to warm to room temperature when the addition was complete. The reaction was stirred at room temperature for 1 hour, and then cooled back to 0° C. and quenched by the addition of a 1:1 THF: H2O mixture (12.4 mL). Et2O was added (50 mL), followed by a 3.6 M solution of NaOH (24.4 mL). The mixture was filtered through Celite, and the solids were washed well with additional Et2O. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound (9.7 g, 97%). The crude compound was used in subsequent steps. 1H NMR (400 MHz, CDCl3) δ 7.38-7.30 (m, 2H), 7.20-7.10 (m, 2H), 2.96 (t, 2H), 2.72 (t, 2H), 1.35 (br s, 2H). MS (ESI) m/z: Calculated: 199; Observed: 200/202 (M++1).

Provenance & Evidence