Water → Ethyl [3-bromo-4-(cyclopropylsulfanyl)phenyl](oxo)acetate
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH:21]1[CH2:23][CH2:22]1.O>ClCCl>[CH2:10]([O:9][C:7](=[O:8])[C:6]([C:18]1[CH:17]=[CH:16][C:15]([S:20][CH:21]2[CH2:22][CH2:23]2)=[C:14]([Br:13])[CH:19]=1)=[O:12])[CH3:11]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of aluminum chloride (40.2 g) in dichloromethane (1200 mL) was added dropwise ethyl chloro(oxo)acetate (32.3 g) at 0° C., followed by stirring at the same temperature for 1 hour. To the reaction mixture was added dropwise a solution of 1-bromo-2-(cyclopropylsulfanyl)benzene (49.3 g) in dichloromethane (280 mL) while keeping it at 5° C. or lower, followed by stirring at room temperature for 1 hour. The reaction mixture was cooled to 0° C., and water was added thereto to stop the reaction. The reaction mixture was extracted with ethyl acetate and the organic layer was sequentially washed with water, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine. The solution was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography to obtain ethyl[3-bromo-4-(cyclopropylsulfanyl)phenyl](oxo)acetate (29.8 g).
Workup
- customat 5° C.
- stirringby stirring at room temperature for 1 hour
- customthe reaction
- extractionThe reaction mixture was extracted with ethyl acetate
- washthe organic layer was sequentially washed with water
- dry with materialThe solution was dried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-984d21cb8921458497f5da18cbbad558
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329707B2
Reaction notes
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