4-Bromo-2-fluoro-1-nitrobenzene → 5-bromo-N-methyl-2-nitroaniline
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.Cl.[CH3:13][NH2:14]>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[NH:14][CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 4-bromo-2-fluoro-1-nitrobenzene (10 g, 45.7 mmol) in DMSO (50 mL) was added TEA (18.47 g, 183 mmol), methylamine hydrochloride (6.1 g, 91.4 mmol) and the reaction mixture was heated under microwave conditions at 120° C. for 3 h. The mixture was cooled, extracted with ethyl acetate; the combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The crude product was used in next step without further purification. (10.5 g, yield 98%) MS (ESI+) e/z: 231.1.
Workup
- temperatureThe mixture was cooled
- extractionextracted with ethyl acetate
- washthe combined organic extracts were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe crude product was used in next step without further purification
Sources & evidence
- ORD record
- ord-6b3ba38f5d1f43258a0e619c81fcdc20
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221794B2
Reaction notes
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