4-Methyl-2-nitroaniline → 2-Bromo-4-methyl-6-nitroaniline
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]Br>CC(O)=O.O>[Br:12][C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]=1[NH2:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
The title compound was prepared by dissolving 4-Methyl-2-nitro-phenylamine (20.0 g, 131 mmol) in 200 mL of HOAc. The reaction mixture was then heated to 100° C. until reaction mixture was homogeneous. At this point the reaction mixture was cooled to room temperature and Br2 (25.21 g, 157 mmol) was added drop wise over the course of 10 minutes. An orange solid formed, and upon completion of the addition the reaction mixture was diluted with water and the title compound collected by filtration (29 g, 96%).
Workup
- temperatureAt this point the reaction mixture was cooled to room temperature
- customAn orange solid formed
- additionupon completion of the addition the reaction mixture
- filtrationthe title compound collected by filtration (29 g, 96%)
Sources & evidence
- ORD record
- ord-21b61d21af0c42aeae25fad031b4b819
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338605B2
Reaction notes
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