Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]=2)C#N)=[CH:4][CH:3]=1>Br>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[N:13]=2)=[O:22])=[CH:6][CH:7]=1Participants
3
Procedure
A slurry of 2-(4-fluoro-phenyl)-3-oxo-3-(6-tri fluoromethyl-pyridin-2-yl)-propionitrile (1.4 g, 4.4 mmol) in 48% HBr is warmed to reflux for 8 h, allowed to stand at ambient temperature 16 h, then warmed at reflux for 8 h. The mixture is extracted with ether, treated with a small amount of sodium bicarbonate, extracted with ether, made basic with solid sodium hydroxide, and extracted again with ether. Ethereal extracts are combined, dried over magnesium sulfate, and concentrated in vacuo to a dark oil. The residual oil is purified on a silica gel cartridge prepared with hexane then eluted with methylene chloride to yield 816 mg (65%) of the title compound as a dark oil.
Workup
- temperatureto reflux for 8 h
- temperaturewarmed
- temperatureat reflux for 8 h
- extractionThe mixture is extracted with ether
- additiontreated with a small amount of sodium bicarbonate
- extractionextracted with ether
- extractionextracted again with ether
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo to a dark oil
- customThe residual oil is purified on a silica gel cartridge
- customprepared with hexane
- washthen eluted with methylene chloride
Sources & evidence
- ORD record
- ord-d6f40288404e4a31815604afe24316b9
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087626B2
Linked notes
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