3-(3-Bromophenyl)propanamide → 3-(3-Bromophenyl)propan-1-amine

To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H).

1. customThe reaction was quenched with the cautious addition of 6 M HCl to pH 1
2. stirringAfter stirring 4 h the solution
3. additionwas adjusted to pH>10 with the addition of 50% aqueous NaOH
4. extractionThis aqueous solution was extracted with EtOAc
5. washThe combined organics were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-f4dfc78902b247c68b45d0fa60a28ec0

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09314467B2