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) was added dropwise to a cooled solution of sulfuryl chloride (96 g, 711 mmol) in DCM (600 mL) at −60° C. The mixture was stirred for 4 h at −20° C., then cooled to −60° C., and 350 mL of EtOH were carefully added. The reaction was then allowed to warm up to rt, subsequently, most of the solvent was evaporated, the residue was poured in sat. aq. NaHCO3, and the solid product was 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 was evaporated
- additionthe residue was poured in sat. aq. NaHCO3
- filtrationthe solid product was filtered off
- washcarefully washed with hexane on the filter
- customair-dried
Sources & evidence
- ORD record
- ord-cb391335bab64dc3bd3bed1711b5ccd0
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524724B2
Reaction notes
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