Ammonia → 3,5-Dibromo-2-(trifluoromethyl)pyridine
Reaction equation
I[C:2]1[C:7]([Br:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[F-].[K+].[F:12][C:13]([Si](C)(C)C)([F:15])[F:14].N>CN1C(=O)CCC1.[Cu]I>[Br:8][C:7]1[C:2]([C:13]([F:15])([F:14])[F:12])=[N:3][CH:4]=[C:5]([Br:9])[CH:6]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-iodo-3,5-dibromopyridine (4.21 g, 11.60 mmol) in NMP (25 mL) were added copper(I) iodide (4.42 g, 23.21 mmol), potassium fluoride (1.35 g, 23.21 mmol), and (trifluoromethyl)trimethylsilane (5.61 mL, 35.90 mmol). The resulting mixture was allowed to stir overnight at 50° C. The mixture was poured into 12% aqueous ammonia, and then extracted with Et2O (2×120 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3,5-dibromo-2-(trifluoromethyl)pyridine (1.63 g, 46%) as a liquid.
Workup
- extractionextracted with Et2O (2×120 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-96c9bdf4dd304fdc937fd480e00dd023
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268992B2
Reaction notes
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