Water → 4-Bromo-2,3-difluoro-6-nitroaniline
Reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[Br:13]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:13][C:7]1[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]([NH2:4])=[C:2]([F:1])[C:8]=1[F:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 3.00 g of 2,3-difluoro-6-nitroaniline in 30 ml of dimethylformamide, 6.14 g of N-bromosuccinimide was added, followed by an hour's stirring at 90° C. Water was added to the reaction liquid which then was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried on anhydrous magnesium sulfate and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (ethyl acetate/hexane=1/6) to provide 3.21 g of the title compound.
Workup
- waitfollowed by an hour
- extractionthen was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried on anhydrous magnesium sulfate
- distillationthe solvent was distilled off
- customThe residue was separated
- custompurified on silica gel column chromatography (ethyl acetate/hexane=1/6)
Sources & evidence
- ORD record
- ord-d29a8d73498f49718b3ea887a037f176
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07125877B2
Reaction notes
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