Nitric Acid → 3-Nitro-4-(trifluoromethoxy)aniline
Reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[N+:13]([O-])([OH:15])=[O:14].[OH-].[NH4+]>S(=O)(=O)(O)O>[N+:13]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1])[NH2:8])([O-:15])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
20 g (112.9 mmol) 4-(trifluormethoxy)-aniline were dissolved in to 50ml conc. sulfuric acid and treated at −5° C. with a mixture of 24 ml conc. sulfuric acid and 6 ml nitric acid. After stirring the mixture at 0° C. for 3 h, the reaction mixture was poured on 1 L ice water and made alkaline with 200 ml conc. aqueous ammonium hydroxide. The resulting solution was extracted with ethyl acetate, the combined organic phases were dried and evaporated to dryness. The residue was purified by flash chromoatography (Silica gel, methylene chloride:methanol=98: 2) and subsequent recrystallization from methylenchoride/heptane. Yield: 14.8 g
Workup
- extractionThe resulting solution was extracted with ethyl acetate
- customthe combined organic phases were dried
- customevaporated to dryness
- customThe residue was purified by flash chromoatography (Silica gel, methylene chloride:methanol=98: 2) and subsequent recrystallization from methylenchoride/heptane
Sources & evidence
- ORD record
- ord-e36eabc5d78749a38eed7951ffdf9994
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759379B2
Reaction notes
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