5-Fluoro-2-nitrophenol → 5-Fluoro-2-nitroanisole
Reaction equation
[C:1]1(NC2C=CC=CC=2)C=CC=CC=1.CC([O-])(C)C.[K+].[F:20][C:21]1[CH:22]=[CH:23][C:24]([N+:28]([O-:30])=[O:29])=[C:25]([OH:27])[CH:26]=1>CN1CCN(C)C1=O>[CH3:1][O:27][C:25]1[CH:26]=[C:21]([F:20])[CH:22]=[CH:23][C:24]=1[N+:28]([O-:30])=[O:29]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
5.4 g (32.1 mmol) of diphenylamine was dissolved in 50 ml of 1,3-dimethyl-2-imidazolidinone (DMI) and stirred under cooling in an ice-bath. Next, 3.6 g (32.1 mmol) of t-BuOK was added thereto. Subsequently, 5.0 g (29.2 mmol) of 2-methoxy-4-fluoronitrobenzene (obtained by methylation of commercially available 5-fluoro-2-nitrophenol) dissolved in 5 ml of DMI was dropped thereinto. After the completion of the dropping, the ice-bath was taken off and the mixture was allowed to stand at room temperature overnight. Next, the liquid reaction mixture was poured into water and extracted with ethyl acetate thrice. After washing with water, drying and concentrating under reduced pressure, the residue was recrystallized from methanol containing a small amount of acetonitrile. Thus, 6.0 g (yield 65%) of the compound (II-2) (2-methoxy-4-diphenylaminonitrobenzene) could be obtained as yellow powdery crystals.
Workup
- temperatureunder cooling in an ice-bath
Sources & evidence
- ORD record
- ord-75da74dc501947ad9cce1f279b739e60
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313349B1
Reaction notes
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