Methanesulfonyl chloride → 1-(Ethenesulfonyl)-4-methoxybenzene
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13]O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CS(Cl)(=O)=O>C(Cl)Cl.C(N(CC)CC)C>[CH:12]([S:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)(=[O:11])=[O:10])=[CH2:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(4-methoxybenzenesulfonyl)ethanol (20 mmol) in dry DCM (20 mL), triethylamine (4 mL) was added. The reaction mixture was cooled to 0° C. followed by dropwise addition of methanesulfonyl chloride (3 mL). The reaction mixture was then stirred at room temperature for 12 h after which it was diluted with DCM (150 mL). The organic phase was washed with 10% aqueous HCl (50 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with hexanes/EtOAc (3:1 to 1:1) to give 5-ethenesulfonyl-2-methoxybenzene (3 g).
Workup
- washThe organic phase was washed with 10% aqueous HCl (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThe residue obtained
- customwas purified by flash column chromatography
- washeluting with hexanes/EtOAc (3:1 to 1:1)
Sources & evidence
- ORD record
- ord-9443f11654a94ba0a19cdd42b3293e88
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582673B2
Reaction notes
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