Bromine → HCID 86710020, compound
Reaction equation
[CH:1]1([CH2:7][CH2:8][C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:14]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[Br:14][CH:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
3-Cyclohexyl-1-cyclopropylpropan-1-one (61.0 mg, 0.338 mmol) obtained in step 2 was dissolved in methanol (1.0 mL), and the mixture was cooled to −5° C., and a dilute solution of bromine (0.0200 mL, 0.372 mmol) in methanol (1.0 mL) was slowly dropped to the mixture. After the dropping, the mixture was stirred at room temperature for hours. Under ice-cooled condition, a sodium thiosulfate aqueous solution was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95) to give 2-bromo-3-cyclohexyl-1-cyclopropylpropan-1-one (87.6 mg, quantitative).
Workup
- temperatureUnder ice-cooled condition
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was then evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95)
Sources & evidence
- ORD record
- ord-859380aa73c44876940e2038b28e84fa
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000186B2
Reaction notes
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