N-bromobutanimide → (2-Bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine
Reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].[Br:16]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(#N)C>[Br:16][C:8]1[CH:7]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[NH:2][CH3:1]Participants
5
Procedure
To a mixture of methyl-(2-nitro-4-trifluoromethyl-phenyl)-amine (16 g) and acetonitrile (200 ml) was added N-bromosuccinimide (15 g) while ice-cooling. The reaction mixture was stirred at room temperature for 5 hours. To the resulting reaction mixture was poured saturated aqueous sodium hydrogen carbonate solution, and then the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give (2-bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine (15 g).
Workup
- temperaturecooling
- customTo the resulting reaction mixture
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d1d096e199934618b2a54173d1192808
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018134B2
Reaction notes
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