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) in a mixture of dichloromethane (600 mL) and acetic acid (200 mL) was slowly added bromine (13 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at ambient temperature for 16 hours. The reaction mixture was concentrated and the concentrate partitioned between ethyl acetate (500 mL) and sodium bicarbonate solution (500 mL). The organic phase was washed with sodium bisulphite solution (400 mL) and concentrated. The concentrate was recrystallized from hexanes containing some dichloromethane.
Workup
- customat 0° C
- concentrationThe reaction mixture was concentrated
- customthe concentrate partitioned between ethyl acetate (500 mL) and sodium bicarbonate solution (500 mL)
- washThe organic phase was washed with sodium bisulphite solution (400 mL)
- concentrationconcentrated
- customThe concentrate was recrystallized from hexanes containing some dichloromethane
Sources & evidence
- ORD record
- ord-6e757f9ef6c8424488ec7e3698738324
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697736B2
Reaction notes
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