Hydrochloric Acid → 3-Bromo-2-methyl-6-nitroaniline
Reaction equation
[Br:1][C:2]1[C:3]([CH3:18])=[C:4]([NH:11]C(=O)C(F)(F)F)[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].O.Cl>CO>[Br:1][C:2]1[C:3]([CH3:18])=[C:4]([C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1)[NH2:11]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
A solution of N-(3-bromo-2-methyl-6-nitrophenyl)-2,2,2-trifluoroacetamide (1.3 g, 3.97 mmol) in CH3OH (30 mL) was treated with potassium carbonate (1.099 g, 7.95 mmol), and the mixture was stirred at 50° C. overnight. The mixture was cooled to room temperature and poured into water, 1N aq HCl was added to adjust to pH 6, and the mixture was extracted with CH2Cl2 (3×). The combined extracts were dried over Na2SO4, and the drying agent was filtered off and solvent was removed in vacuo to give the title compound as a yellow solid (0.57 g, 62%).
Workup
- temperatureThe mixture was cooled to room temperature
- additionwas added
- extractionthe mixture was extracted with CH2Cl2 (3×)
- dry with materialThe combined extracts were dried over Na2SO4
- filtrationthe drying agent was filtered off
- customsolvent was removed in vacuo
Sources & evidence
- ORD record
- ord-da29824970f44042995a26f3e844d2c8
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937150B2
Reaction notes
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