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-8d5660706f2a47a9ae9eec2bbc6e2a8d

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299307B2