Morpholine → 4-(3,5-Difluoro-4-nitro-phenyl)-morpholine
Reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([F:9])[C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:5]=[C:4]([F:9])[C:3]=1[N+:10]([O-:12])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
2,4,6-Trifluoronitrobenzene (4.95 g) and potassium carbonate (4.63 g) were mixed in dry dimethyl sulfoxide (40 mL) and cooled to 10° C. under argon. Morpholine (2.56 mL) was added and the reaction mixture was allowed to warm to 25° C. and stirred under argon for 16 hours. The reaction mixture was concentrated in vacuo Brine (50 mL) was added and the product was extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo). The crude material was purified by flash chromatography to furnish 2.49 g (37% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6): 3.43 (t, 4H), 3.69 (t, 4H), 6.87 (d, 2H).
Workup
- temperatureto warm to 25° C.
- concentrationThe reaction mixture was concentrated in vacuo Brine (50 mL)
- additionwas added
- extractionthe product was extracted with ethyl acetate (3×50 mL)
- dry with materialThe combined organic phases were dried over magnesium sulfate
- concentrationconcentrated in vacuo)
- customThe crude material was purified by flash chromatography
Sources & evidence
- ORD record
- ord-5fd85760e2ab442bb81d5387918cffd1
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012962B2
Reaction notes
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