Water → 2-(4-Fluoro-2-nitrophenyl)-N,N-dimethylethen-1-amine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16].C(OCC)C.O>CN(C=O)C>[CH3:14][N:15]([CH:17]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[CH3:16]Participants
6
Conditions
- Temperature
- 140 °C
Procedure
To a solution of 4-fluoro-2-nitrotoluene (5 g, 32 mmol) in DMF (32 ml) was added dimethylformamide dimethyl acetal (5.56 ml, 42 mmol) and the mixture warmed at 140° C. for 18 hours in Argon atmosphere. Then the solution was allowed to reach room temperature and diethyl ether (100 ml) and water (100 ml) was added. The organic layer was washed with water (2×100 ml) and brine (1×100 ml), dried (MgSO4) and solvent concentrated at reduced pressure, affording N,N-dimethyl-2-(4-fluoro-2-nitrophenyl)ethenylamine as a red solid. No further purification was necessary.
Workup
- customto reach room temperature
- washThe organic layer was washed with water (2×100 ml) and brine (1×100 ml)
- dry with materialdried (MgSO4) and solvent
- concentrationconcentrated at reduced pressure
Sources & evidence
- ORD record
- ord-bea888ab557e45fba817523417483464
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05929072
Reaction notes
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