Triphenylphosphine → 2-Amino-1-(3-bromophenyl)ethan-1-ol

Temperature

50 °C

To a solution of 2-Azido-1-(3-bromo-phenyl)-ethanol (3.38 g, 13.8 mmol) in THF (40 mL) was added water (2.48 ml, 138 mmol) and triphenylphosphine (7.26 g, 27.7 mmol). The mixture stirred for 2 hours at 50° C. and was then cooled to room temperature, diluted with water and extracted with ethyl acetate. The organics were washed with 1M HCl (2×) and the aqueous washes were combined and neutralized with 1N sodium hydroxide. The aqueous mixture was extracted with ethyl acetate and the organics were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The title compound was isolated as a yellow oil (2.53 g, 85%). 1H NMR (300 MHz, CDCl3): 7.55 (s, 1H), 7.41 (d, 1H), 7.31-7.20 (m, 2H), 4.62 (m, 1H), 3.02 (d, 1H), 2.79 (m, 1H).

1. temperaturewas then cooled to room temperature
2. extractionextracted with ethyl acetate
3. washThe organics were washed with 1M HCl (2×)
4. extractionThe aqueous mixture was extracted with ethyl acetate
5. washthe organics were washed with water and brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-219397158caf4ab1803d93c55d917f5c

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816354B2