Water → 3-fluoro-N-(4-methoxyphenyl)-2-nitroaniline
Reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:8][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
20.0 g (126 mmol) of 2,6-difluoronitrobenzene and 17.0 g (138 mmol) of p-anisidine were dissolved in N,N-dimethylformamide (60 ml), and 20.8 g (150 mmol) of potassium carbonate was added thereto. The mixture was heated with stirring for 12 hours at 75° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The extracted organic layer was washed with water, 10% hydrochloric acid, water, and a saturated aqueous solution of sodium chloride in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:9), to obtain 21.2 g (yield: 64%) of 3-fluoro-N-(4-methoxyphenyl)-2-nitroaniline as a brown liquid.
Workup
- temperatureThe mixture was heated
- extractionextracted with ethyl acetate
- washThe extracted organic layer was washed with water, 10% hydrochloric acid, water
- dry with materiala saturated aqueous solution of sodium chloride in this order, dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue thus obtained
- customwas purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:9)
Sources & evidence
- ORD record
- ord-32478bc9497745548bc000700d20adbd
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389523B2
Reaction notes
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