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 (19.76 g, 126 mmol) in a mixture of dichloromethane (600 mL) and acetic acid (200 mL) was slowly added bromine (15 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at ambient temperature for 20 hrs. The mixture was concentrated and the residue partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase was separated, washed with sodium bisulphite solution and concentrated. The residue was recrystallized from hexanes containing some dichloromethane to provide 22.7 g (76%) of the title compound. 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
- customThe organic phase was separated
- washwashed with sodium bisulphite solution
- concentrationconcentrated
- customThe residue was recrystallized from hexanes containing some dichloromethane
Sources & evidence
- ORD record
- ord-eea5117349124694aa193cb584d855a4
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07999117B2
Reaction notes
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