Sulfuric Acid → 3-Bromophenethylamine

Temperature

-5 °C

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).

1. temperatureto warm to room temperature when
2. additionthe addition
3. stirringThe reaction was stirred at room temperature for 1 hour
4. temperaturecooled back to 0° C.
5. customquenched by the addition of a 1:1 THF
6. additionEt2O was added (50 mL)
7. filtrationThe mixture was filtered through Celite
8. washthe solids were washed well with additional Et2O
9. dry with materialThe organic phase was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-e48ea1ae7cfb4b77a991190958bb3c49

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919519B2