2-Bromo-1-ethyl-4-nitrobenzene → 3-Bromo-4-ethylaniline
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][CH3:12]>CO.[Ni]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH2:11][CH3:12])[NH2:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-bromo-1-ethyl-4-nitro-benzene (25 g, 0.019 mol) in MeOH (100 mL) was added Raney-Ni (2.5 g). The reaction mixture was hydrogenated under hydrogen (1 atm) at room temperature. After stirring for 3 hours, the mixture was filtered and concentrated under reduced pressure. The crude material was purified by preparative HPLC to give 3-bromo-4-ethylaniline (8.0 g, 48%). 1H NMR (400 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1H), 6.83 (d, J=2.4 Hz, 1H), 6.52 (dd, J=2.4, 8.4 Hz, 1H), 2.57 (q, J=7.6 Hz, 2H), 1.10 (t, J=7.6 Hz, 3H). MS (ESI) m/e (M+H+) 200.
Workup
- customwas hydrogenated under hydrogen (1 atm) at room temperature
- filtrationthe mixture was filtered
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-4be28b5c5e074c6e9aa05f050d7cc607
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691902B2
Reaction notes
Loading…