4-Nitrophenol → 1-(1,1,2,3,3,3-Hexafluoropropoxy)-4-nitrobenzene
Reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.O.[K].CN(C)C=O.[F:18][C:19]([F:26])([F:25])[C:20]([F:24])=[C:21]([F:23])[F:22]>O.C(OCC)(=O)C>[F:22][C:21]([F:23])([O:10][C:3]1[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=1)[CH:20]([F:24])[C:19]([F:26])([F:25])[F:18]Participants
7
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 4.63 g of p-nitrophenol and 0.56 g of potassium hydrate added to 100 ml of N,N-dimethylformamide blowed hexafluoropropene at room temperature, and then the solution was stirred at 50° C. for 1 hour. Next, ethyl acetate and water were introduced in the reaction solution for separating the organic phase. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under a reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:EtOAc=20:1) to obtain 3.81 g of the desired product (Yield: 42%) as a yellow oil.
Workup
- customat room temperature
- customfor separating the organic phase
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- customthe solvent was removed under a reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (n-hexane:EtOAc=20:1)
Sources & evidence
- ORD record
- ord-746c4d7cf3d848e2befd053d5d04fc02
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067638B2
Reaction notes
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