Sodium Hydroxide → 4-bromo-2-nitro-5-(trifluoromethyl)aniline
Reaction equation
[Br:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12]C(=O)C)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5]([NH2:12])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of the acetamide from step (b) above (4.5 g, 14 mmol) in MeOH (8 mL) was added aqueous 3N NaOH (50 mL) at room temperature. The reaction mixture was stirred at 90° C. for 2 h, cooled to room temperature and extracted with EtOAc (4×50 mL). The combined organic extracts were washed with 1% aqueous HCl and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (15% EtOAc/hexane) to give the title compound as a yellow solid. MS (ESI, neg. ion) m/z: 282.9 (M−1).
Workup
- temperaturecooled to room temperature
- extractionextracted with EtOAc (4×50 mL)
- washThe combined organic extracts were washed with 1% aqueous HCl and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (15% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-44d7627c5fd140aa966549de5e7376a7
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026241B2
Reaction notes
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