Bromine → 2-Bromo-5-nitro-4-(trifluoromethyl)aniline
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[NH2:7])([O-:3])=[O:2].[Br:15]Br>CC(O)=O>[Br:15][C:8]1[CH:9]=[C:10]([C:11]([F:12])([F:13])[F:14])[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[NH2:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 3-nitro-4-(trifluoromethyl)aniline (31.0 g, 150.4 mmol) in HOAc (200 mL) was added bromine (9.3 mL, 180.5 mmol) at 0° C. under an atmosphere of N2. The cooling bath was removed and the mixture was stirred at 20° C. for 1 h. The solvent was removed in vacuo to afford the crude product 2-bromo-5-nitro-4-(trifluoromethyl)aniline (40.0 g, 93%), which was used directly in the next step.
Workup
- customThe cooling bath was removed
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-96026347b21a4ccda75f3575ce79e741
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802700B2
Reaction notes
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