Acetic Acid → 2-Bromo-5-methoxyaniline
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O.C(O)C.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1-bromo-4-methoxy-2-nitrobenzene (10 g; 43.1 mmol), ethanol (100 ml), acetic acid (100 ml) and iron powder (9.63 g; 172 mmol) was heated at 100° C. for 2 h. The mixture was cooled to room temperature and diluted with water (300 ml). The suspension was neutralized with solid potassium carbonate. The mixture was filtered on a plug of celite and extracted with dichloromethane. The combined organic layers were dried over magnesium sulphate and concentrated under reduced pressure to afford 2-bromo-5-methoxyaniline, which was used in the next step without further purification.
Workup
- temperatureThe mixture was cooled to room temperature
- filtrationThe mixture was filtered on a plug of celite
- extractionextracted with dichloromethane
- dry with materialThe combined organic layers were dried over magnesium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-150a14767a0d4d92921a2cd32c94c892
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785638B2
Reaction notes
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