m-Chloroperbenzoic acid → 1-Nitro-3-[(propan-2-ylsulfonyl)methyl]benzene

HRID 514702Notes

Reaction equation

HRID 514702 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]SC(C)C)[CH:5]=1)([O-:3])=[O:2].Cl[C:16]1[CH:21]=CC=C(C(OO)=O)[CH:17]=1.[S:26]([O-:29])(O)=[O:27].[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][S:26]([CH:16]([CH3:21])[CH3:17])(=[O:29])=[O:27])[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 709764371-Nitro-3-[(propan-2-ylsulfanyl)methyl]benzene

Product 1

HCID 225020781-Nitro-3-[(propan-2-ylsulfonyl)methyl]benzene

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-nitro-3-[(propan-2-ylsulfanyl)methyl]benzene (4.0 g) in DCM (160 mL) was treated at 0° C. with portions of m-chloroperbenzoic acid (9.3 g, 77%). The mixture was stirred at 0° C. for further 30 minutes and then 18 hours at room temperature. The reaction mixture was diluted with DCM before sodium hydrogen sulfite and sodium bicarbonate solution was added and extracted with DCM (2×). The combined organic phases were washed and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 12%-100%) to give the title compound (4.5 g).

Workup

  1. custom18 hours
  2. customat room temperature
  3. additionwas added
  4. extractionextracted with DCM (2×)
  5. washThe combined organic phases were washed
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (hexane/ethyl acetate 12%-100%)

Sources & evidence

ORD record
ord-7b14bccc2ec14df88c74b110fb8359d7
Source dataset
uspto-grants-2015_08
Patent number
US09108926B2

Reaction notes

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