Methyl bromoacetate → Methyl 2-(4-chlorobenzenesulfonyl)acetate
Reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[Na+]>CN(C=O)C.O>[CH3:6][O:5][C:3](=[O:4])[CH2:2][S:14]([C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)(=[O:16])=[O:15]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of methyl bromoacetate (11.25 ml, 116 mmol) and sodium 4-chloro-benzenesulfinate (25.2 g, 116 mmol) in DMF (120 ml) was stirred and heated at 80° C. for 2 h. The solution was diluted with water (360 ml). The separated oil was extracted with chloroform (200 ml) and washed with water (3×80 ml). The organic phase was evaporated in vacuo to obtain 22.4 g of the title compound in 77.7% yield.
Workup
- extractionThe separated oil was extracted with chloroform (200 ml)
- washwashed with water (3×80 ml)
- customThe organic phase was evaporated in vacuo
Sources & evidence
- ORD record
- ord-919911c841f84e6e8ebce34d834a3a29
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063220B2
Reaction notes
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