(Trifluoromethyl)trimethylsilane → 1-(6-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-ol
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[Si]([C:14]([F:17])([F:16])[F:15])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O.[Cl-].[Na+].O>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[C:14]([F:17])([F:16])[F:15])[CH:5]=[CH:4][CH:3]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
6-Bromopyridine-2-carbaldehyde (1.0 g, 5.38 mmol) was taken up in 35 mL THF and cooled to 0° C. TMSCF3 (1.0 mL, 6.45 mmol) was added followed by tetrabutylammonium fluoride (6.45 mL of 1.0M in THF). The reaction was stirred allowed to warm to room temperature and maintained at that temperature for 4.5 hours. The mixture was then diluted with water and brine, and extracted with ethyl acetate (3×). The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (0-40% ethyl acetate/hexanes) afforded the title compound.
Workup
- temperatureto warm to room temperature
- temperaturemaintained at that temperature for 4.5 hours
- extractionextracted with ethyl acetate (3×)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customPurification by silica gel chromatography (0-40% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-c027576ca8d34dd3b7e6acf0e1e723d2
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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