Bromine → 2-Bromo-4-fluoro-6-nitroaniline
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]Br>ClCCl.C(O)(=O)C>[Br:12][C:7]1[CH:8]=[C:2]([F:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]=1[NH2:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-fluoro-2-nitroaniline (20 g, 128 mmol) in dichloromethane (600 mL) and acetic acid (200 mL) was slowly added bromine (13 mL, 256 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour and at ambient temperature for 16 hours. The mixture was concentrated and the residue partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase was washed with sodium bisulphite solution and concentrated and the residue recrystallized from hexane/dichloromethane to provide the title compound (22.7 g, 76%). MS (DCI/NH3) m/z 236 (M+H)+.
Workup
- customat 0° C
- concentrationThe mixture was concentrated
- customthe residue partitioned between ethyl acetate and sodium bicarbonate solution
- washThe organic phase was washed with sodium bisulphite solution
- concentrationconcentrated
- customthe residue recrystallized from hexane/dichloromethane
Sources & evidence
- ORD record
- ord-0b803e0d54764b89a31f88eb3844d390
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462724B2
Reaction notes
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