Potassium Carbonate → 2-Bromo-1-(3-pyridyl)-1-butanone
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[O:11])[CH2:8][CH2:9][CH3:10])[CH:2]=1.[Br:12]Br.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>Br.C(O)(=O)C>[Br:12][CH:8]([CH2:9][CH3:10])[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:11]Participants
7
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 1-(3-pyridyl)-1-butanone (20.0 g) in 47% aqueous hydrobromic acid (40 ml) and acetic acid (40 ml) was added bromine (15.2 ml), and the mixture was stirred at 60° C. for 30 minutes. The reaction mixture was poured into ice-water, and after adding a saturated aqueous sodium thiosulfate solution, potassium carbonate was added to the mixture to adjust pH to 4. The reaction mixture was extracted with ethyl acetate, washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product of 2-bromo-1-(3-pyridyl)-1-butanone (30.15 g) as brownish oil.
Workup
- additionwas added to the mixture
- extractionThe reaction mixture was extracted with ethyl acetate
- washwashed successively with a saturated aqueous sodium hydrogen carbonate solution and brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-2ae6d71b1c624959b034eff3138e9928
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759373B2
Reaction notes
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