Ammonium Chloride → 3-Bromo-5-fluoro-2-methylaniline
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12].[NH4+].[Cl-]>O.C(O)(C)C.[Fe]>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([NH2:9])[CH:5]=[C:6]([F:8])[CH:7]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
To iron powder (325 mesh, 2.25 g, 40.3 mmol) in 30 ml water and 80 ml isopropanol was added commercially available 1-bromo-5-fluoro-2-methyl-3-nitro-benzene (3.04 g, 13 mmol) in 45 ml isopropanol and NH4Cl (1.46 g, 27.3 mmol). The resulting mixture was heated at 110° C. for 2 h. After evaporation of most of the isopropanol the aq solution was extracted with ethyl acetate three times. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and evaporated. The crude product was used without further purification in the next step.
Workup
- customAfter evaporation of most of the isopropanol the aq solution
- extractionwas extracted with ethyl acetate three times
- washThe combined organic layers were washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customThe crude product was used without further purification in the next step
Sources & evidence
- ORD record
- ord-e6322d2c07c0442eb0a7e6b983a5a71a
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378092B2
Reaction notes
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