Water → 1-(2-Nitro-vinyl)-4-trifluoromethyl-benzene
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C([O-])(=O)C.[NH4+].O.[N+:19]([CH3:22])([O-:21])=[O:20]>>[N+:19]([CH:22]=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=1)([O-:21])=[O:20]Participants
5
Procedure
4-Trifluoromethylbenzaldehyde (3.00 g, 17.2 mmol) was dissolved in nitromethane (10 ml), to which ammonium acetate (1.341 g, 17.4 mmol) was added, and the mixture was heated under reflux for 2 hours. Water was added to the mixture, which was extracted with methylene chloride twice, and the extracts were combined and washed with brine, and dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1) to afford 1-(2-nitrovinyl)-4-trifluoromethylbenzene (1.596 g, yield 43%) as a pale yellow crystalline powder.