Water → Ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate
Reaction equation
[C:1]([C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:12]Br.O>C(O)C>[Br:12][CH2:2][C:1]([C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1)=[O:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
Ethyl 1-acetylcyclopropanecarboxylate (200 g, 1.28 mol) was dissolved in ethanol (1000 ml), and bromine (72.7 ml, 1.41 mol) was added dropwise while stirring and cooling with ice. After completion of dripping, the temperature of the reaction solution was raised to 30° C. and stirring was performed for 2 hours. After adding water (1000 ml) to the reaction solution while cooling with ice, it was concentrated under a reduced pressure was performed. After extracting the concentrate into ethyl acetate (750 ml×2), it was washed with a 10% aqueous sodium thiosulfate solution (500 ml×2) and saturated sodium bicarbonate water (500 ml×2) in that order and then dried over anhydrous sodium sulfate. After filtering and concentrating the filtrate under a reduced pressure, 291 g (97%) of the title compound was obtained as a yellow, oily substance.
Workup
- temperaturecooling with ice
- stirringstirring
- temperaturewhile cooling with ice, it
- concentrationwas concentrated under a reduced pressure
- extractionAfter extracting the
- concentrationconcentrate into ethyl acetate (750 ml×2), it
- washwas washed with a 10% aqueous sodium thiosulfate solution (500 ml×2) and saturated sodium bicarbonate water (500 ml×2) in that order
- dry with materialdried over anhydrous sodium sulfate
- filtrationAfter filtering
- concentrationconcentrating the filtrate under a reduced pressure
Sources & evidence
- ORD record
- ord-14d453d5216a470fa0ca08ac7c2dccc1
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902226B2
Reaction notes
Loading…