Dimethylformamide → 1-[2-nitro-4-(trifluoromethyl)phenyl]pyrrolidine
Reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.F[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]>O>[N+:22]([C:13]1[CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:16]=[CH:17][C:12]=1[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:24])=[O:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Pyrrolidine ((983 μl, 12.0 mmol, commercially available product) was added at 0° C. to a N,N-dimethylformamide (DMF; 4 ml) solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (1.02 g, 4.89 mmol, commercially available product). The resulting mixture was warmed to room temperature and stirred for 4.5 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=5/1). Thus, 1-[2-nitro-4-(trifluoromethyl)phenyl]pyrrolidine (1.26 g, 99.3%) was yielded as an orange-colored solid.
Workup
- extractionthe resulting mixture was extracted three times with ethyl acetate
- washThe obtained organic layer was washed with a saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=5/1)
Sources & evidence
- ORD record
- ord-00871bc5d4f44951be967fea37134eaa
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08816089B2
Reaction notes
Loading…