Formic Acid → Methyl 2-(3-chloro-4-(methylsulfonyl)phenyl)propanoate
Reaction equation
C(O)=[O:2].[Cl:4][C:5]1[CH:6]=[C:7]([CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][C:10]=1[S:11][CH3:12].OO.C(OCC)(=O)C.CCCCCC.[OH2:33]>>[Cl:4][C:5]1[CH:6]=[C:7]([CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][C:10]=1[S:11]([CH3:12])(=[O:2])=[O:33]Participants
Conditions
- Temperature
- 0 °C
Procedure
Formic acid (20.8 mL, 1 eq) was added to methyl 2-(3-chloro-4-(methylthio)phenyl)propanoate (3.2 g, crude) and cooled to 0° C. Hydrogen peroxide (4.48 mL, 3 eq) was added drop wise at 0° C. and the reaction mass was stirred for overnight at room temperature. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane, Rf˜0.3). On completion of the reaction, the contents were cooled to 0° C., water was added and the mixture was extracted with ethyl acetate (2×100 mL). The combined extract was washed with NaHCO3 solution, dried over sodium sulfate and concentrated under reduced pressure to obtain methyl 2-(3-chloro-4-(methylsulfonyl)phenyl)propanoate as a colorless thick liquid (3.2 g, crude). Crude product obtained was directly used for the next step.
Workup
- customOn completion of the reaction
- temperaturethe contents were cooled to 0° C.
- extractionthe mixture was extracted with ethyl acetate (2×100 mL)
- extractionThe combined extract
- washwas washed with NaHCO3 solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5652495a18a94bc29362de670cb781be
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946204B2
Reaction notes
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