4-Tert-butyl-2-chloro-5-nitro-phenol → 4-Tert-butyl-2-chloro-5-amino-phenol
Reaction equation
[C:1]([C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([OH:14])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([OH:14])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-tert-butyl-2-chloro-5-nitro-phenol (12.6 g, 54.9 mmol) in MeOH (50 mL) was added Ni (1.2 g). The reaction was shaken under H2 (1 atm) for 4 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (P.E./EtOAc, 20:1) to give 4-tert-butyl-2-chloro-5-amino-phenol (C-11) (8.5 g, 78%). 1H NMR (DMSO-d6) δ 9.33 (s, 1H), 6.80 (s, 1H), 6.22 (s, 1H), 4.76 (s, 1H), 1.23 (s, 9H); ESI-MS 200.1 m/z (MH+).