Hydrochloric Acid → 3-Amino-1-(3-bromophenyl)propan-1-ol

To a solution of 3-(3-bromophenyl)-3-hydroxypropanenitrile (23) (117.5 g, 519.8 mmol) in anhydrous THF (300 mL) under argon borane-methylsulfide (68 mL, 675.7 mmol) was slowly added over 30 min via a dropping funnel. The reaction mixture was boiled under reflux for 2.5 hr and cooled to room temperature. HCl solution (1.25M in EtOH, 350 mL) was slowly added for 30 min and the mixture was concentrated under reduced pressure. Water (400 mL) was added and the pH of the mixture was then adjusted to 12 with aqueous NaOH (50% wt). The product was extracted with CH2Cl2 (500 mL), the extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give hydroxyamine 24 as a colorless oil. Yield (104 g, 87%). 1H NMR (400 MHz, DMSO-d6) δ 7.49 (m, 1H), 7.37 (dt, J=7.2, 1.6 Hz, 1H), 7.23-7.31 (m, 2H), 4.66 (t, J=6.8 Hz, 1H), 2.61 (m, 2H), 1.61 (q, J=6.8 Hz, 2H).

1. temperatureunder reflux for 2.5 hr
2. concentrationthe mixture was concentrated under reduced pressure
3. additionWater (400 mL) was added
4. extractionThe product was extracted with CH2Cl2 (500 mL)
5. dry with materialthe extract was dried over anhydrous Na2SO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-82692e7993414e80ae4796d8e8ae0d94

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492589B2