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2-amino-1-(3-bromophenyl)ethan-1-ol synthesis

4synthesis methods
Benzenemethanol, α-(azidomethyl)-3-bromo-

943911-72-6
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Yield:41147-81-3 85%

Reaction Conditions:

with water;triphenylphosphine in tetrahydrofuran at 50; for 2 h;

Steps:

22

To a solution of 2-Azido-l-(3-bromo-phenyl)-ethanol (3.38g, 13.8mmol) in THF (4OmL) was added water (2.48ml, 138mmol) and triphenylphosphine (7.26g, 27.7mmol). The mixture stirred for 2 hours at 5O0C and was then cooled to room temperature, diluted with water and extracted with ethyl acetate. The organics were washed with IM HCl (2x) and the aqueous washes were combined and neutralized with IN 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 (2.53g, 85 %). 1H NMR (300 MHz, CDCl3): 7.55 (s, IH), 7.41 (d, IH), 7.31-7.20 (m, 2H), 4.62 (m, IH), 3.02 (d, IH), 2.79 (m, IH).

References:

WO2007/78523,2007,A2 Location in patent:Page/Page column 71