Water → HCID 4772457, compound
Reaction equation
[F-].[K+].[O:3]=[CH:4][C:5]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[C:7]([OH:8])[CH:6]=1.F[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].O>CS(C)=O>[N+:25]([C:16]1[CH:17]=[C:18]([C:21]([F:22])([F:23])[F:24])[CH:19]=[CH:20][C:15]=1[O:8][C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][C:9]=1[O:10][CH3:11])[CH:4]=[O:3])([O-:27])=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a stirred suspension of potassium fluoride (457 mg, 7.8 mmol) in dry DMSO (20 ml) was added a solution of isovanillin (1.0 gm, 6.57 mmol) in dry DMSO (20 ml). The reaction contents were heated at 140° C. for 10 min. A solution of 4-fluoro-3-nitrobenzotrifluoride (1.37 gm, 6.57 mmol) in dry DMSO (10 ml) was added to the above suspension and the reaction mixture was stirred at 140° C. for 4.0 h. The reaction mixture was cooled to room temperature and the contents were poured into water (200 ml) and extracted with ethyl acetate (100 ml×3). The organic extracts were combined and washed with 1N sodium hydroxide (50 ml×2), water and brine and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo to obtain 3-(2-nitro-4-trifluoromethyl phenoxy)-4-methoxy benzaldehyde as a pale yellow solid (2.0 gm).
Workup
- customThe reaction contents
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate (100 ml×3)
- washwashed with 1N sodium hydroxide (50 ml×2), water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationThe organic layer was concentrated in vacuo
Sources & evidence
- ORD record
- ord-36a326aa8ff042479faf71dba81f0958
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238725B2
Reaction notes
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