Acetone → 2-(5-Bromo-3-pyridyl)propan-2-ol
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C([Li])CCC.[CH3:14][C:15]([CH3:17])=[O:16]>C1(C)C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([C:15]([OH:16])([CH3:17])[CH3:14])[CH:3]=[N:4][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added a solution of 3,5-dibromopyridine (264 g, 1.12 mol) in toluene (3000 mL). The solution was cooled to −78° C., and a solution of n-butyllithium in hexanes (2.6 M, 475 mL, 1.24 mol) was then added, giving a solution that was stirred for 2 hours at −78° C. Acetone (108 g, 1.86 mol) was then added. After 1 hour, the reaction mixture was quenched by addition of 350 mL saturated aqueous ammonium chloride solution. The resulting solution was extracted with ethyl acetate. The organic extracts were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography on silica gel (ethyl acetate/petroleum ether 1:10-1:5) provided the title compound: 1H NMR (400 MHz, CDCl3): δ 8.63 (s, 1H), 8.56 (s, 1H), 8.01 (s, 1H), 1.61 (s, 6H).
Workup
- customTo a 5000-mL 4-necked round-bottom flask purged
- temperaturemaintained with an inert atmosphere of nitrogen
- customgiving a solution that
- waitAfter 1 hour
- customthe reaction mixture was quenched by addition of 350 mL saturated aqueous ammonium chloride solution
- extractionThe resulting solution was extracted with ethyl acetate
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customPurification by flash chromatography on silica gel (ethyl acetate/petroleum ether 1:10-1:5)
Sources & evidence
- ORD record
- ord-ea19274b10a4419ebd80b7be40d72c45
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193724B2
Reaction notes
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