4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → 2-Nitro-4-(trifluoromethyl)benzonitrile
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Br-].[Li+].[CH3:17][N:18]1CCCC1=O>>[C:17]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])#[N:18]Participants
Conditions
- Temperature
- 175 °C
Procedure
In a flask were placed 1.13 grams (g) (5.0 mmol) 4-chloro-3-nitrobenzotrifluoride, 0.4478 g (5.0 mmol) cuprous cyanide, 0.4342 g (5.0 mmol) lithium bromide and 10 milliliters (ml) N-methyl-2-pyrrolidinone, under a nitrogen blanket. The reaction mixture was then heated to a temperature of 175° C. and reaction was continued at a range of 172°-178° C. over a period of 24 hours. At the end of that run, the heat source was removed and the reaction mixture cooled. Product was recovered by washing with water, 3M HCl, diethyl ether, again with 3M HCl, and again with ether. The ether extract was dried over magnesium sulfate, filtered and the solvent stripped, yielding 0.875 g (81% of theoretical yield) of an amber, somewhat tarry looking oil, which was identified by gas chromatographic analysis as the desired product.
Workup
- customIn a flask were placed
- customAt the end of that run, the heat source was removed
- temperaturethe reaction mixture cooled
- customProduct was recovered
- washby washing with water, 3M HCl, diethyl ether, again with 3M HCl
- extractionThe ether extract
- dry with materialwas dried over magnesium sulfate
- filtrationfiltered
- customyielding
- custom0.875 g (81% of theoretical yield) of an amber
Sources & evidence
- ORD record
- ord-7092be271b1f4659a9ccf4acfb4957f3
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886936
Reaction notes
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