Ammonium Chloride → Benzenamine, ar-bromo-ar-chloro-

To a solution of 1-bromo-2-chloro-3-nitrobenzene (3.0 g, 12.7 mmol) in MeOH (127 ml) was added Zn dust (8.30 g, 127 mmol) followed by NH4Cl (6.79 g, 127 mmol) which resulted in a significant exotherm. The heterogeneous reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through a pad of Celite and concentrated to an off-white solid. To this solid was added EtOAc and the resulting mixture was sonicated for 10 minutes. The mixture was filtered through Celite and washed with EtOAc. The combine filtrates were concentrated in vacuo to afford 2.17 g (10.5 mmol, 79%) of 3-bromo-2-chloroaniline: LCMS(m/z): 205.9 (MH+); tR=0.87 minute: 1H NMR (400 MHz, CDCl3) δ 6.62-6.66 (m, 1H) 6.87 (t, J=8.0 Hz, 1H) 6.97 (d, J=7.8 Hz, 1H) 7.22 (d, J=9.0 Hz, 1H).

1. customresulted in a significant exotherm
2. filtrationThe reaction mixture was filtered through a pad of Celite
3. concentrationconcentrated to an off-white solid
4. additionTo this solid was added EtOAc
5. customthe resulting mixture was sonicated for 10 minutes
6. filtrationThe mixture was filtered through Celite
7. washwashed with EtOAc
8. concentrationThe combine filtrates were concentrated in vacuo

ORD record

ord-4cb03a0b0c354a399e0b5310e84dc0fb

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242260B2