Ethanol → 1-(Methylsulfinyl)-3-nitrobenzene
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10][CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].S(Cl)(Cl)(=O)=[O:13].CCO>C(Cl)Cl>[CH3:11][S:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of 3-nitro thioanisol (96 g, 568 mmol) in DCM (100 mL) is added dropwise to a cooled solution of sulfuryl chloride (96 g, 711 mmol) in DCM (600 mL) at −60° C. The mixture is stirred for 4 h at −20° C., then cooled to −60° C., and 350 mL of EtOH are carefully added. The reaction is then allowed to warm up to rt, subsequently, most of the solvent is evaporated, the residue is poured in sat. aq. NaHCO3, and the solid product is filtered off and carefully washed with hexane on the filter, then air-dried to give the desired sulfoxide (95 g, 90% yield).
Workup
- temperaturecooled to −60° C.
- temperatureto warm up to rt
- customsubsequently, most of the solvent is evaporated
- additionthe residue is poured in sat. aq. NaHCO3
- filtrationthe solid product is filtered off
- washcarefully washed with hexane on the filter
- customair-dried
Sources & evidence
- ORD record
- ord-531516471b5e4b789771ed0dd2603a9e
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825128B2
Reaction notes
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