Ethyl Acetate → 2-Chloro-4-nitro-6-(trifluoromethyl)aniline
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)([O-:3])=[O:2].[Cl:15]N1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C>[Cl:15][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:11]([F:12])([F:13])[F:14])[C:7]=1[NH2:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
4-Nitro-2-trifluoromethyl-phenylamine (5.6 g) and N-chlorosuccinimide (4.0 g) were suspended in acetonitrile (15 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. Ethyl acetate (80 mL) was added and the organic phase was washed with 5% aqueous NaOH (2×50 mL), water (2×50 mL) and brine (2×50 mL). The organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 4.9 g (75% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, CDCl3): 5.35 (b, 2H), 8.35 (b, 1H), 8.37 (b, 1H).
Workup
- washthe organic phase was washed with 5% aqueous NaOH (2×50 mL), water (2×50 mL) and brine (2×50 mL)
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-674dbe74e19840629c8165815e0c1c87
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632835B2
Reaction notes
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