Dichloromethane → 3-Bromo-4-ethylaniline
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9].C(Cl)Cl>C(O)C.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9])[NH2:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Hydrogenation of 4.45 g (19 mmol) of 3-bromo-4-ethyl-nitrobenzene (for preparation see Macromolecules 1995, 28, 5618) in 100 ml of ethanol in the presence of 1 g of Raney nickel, followed by filtration, concentration by evaporation and chromatography (SiO2; methylenechloride), yields 3-bromo-4-ethyl-aniline; 1H NMR (CDCl3) δ6.94 (d, 1H), 6.82 (s, 1H), 6.50 (d, 1H), 3.50 (s, H2N), 2.57 (q, 2H), 1.10 (t, 3H).
Sources & evidence
- ORD record
- ord-84530c68356c47fe9e4fe9749e53d702
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706731B2
Reaction notes
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