Ethyl Acetate → 1-(Methylsulfonyl)-4-nitrobenzene

HRID 1883001Notes

Reaction equation

HRID 1883001 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](SC)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:13]1C=C(C=CC=1)C(OO)=O.C(OCC)(=O)C.[S:29](=[O:32])(O)[O-:30].[Na+]>C(Cl)(Cl)Cl>[CH3:13][S:29]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:32])=[O:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 961094-Nitrophenyl methyl sulfideHCID 23665763Sodium Bisulfite

Product 1

HCID 2584341-(Methylsulfonyl)-4-nitrobenzeneYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of methyl 4-nitrophenyl sulfide (10 g, 59.1 mmol) in chloroform at 0° C. was added m-chloroperoxybenzoic acid (55.6 g, 177.3 mmol). After 3 h, ethyl acetate (1.2 L) was added followed by satd aq sodium bisulfite. After stirring overnight, the layers were separated and the organic phase was washed with satd ag sodium bicarbonate (3×200 mL), followed by brine, and then dried over MgSO4, filtered and concentrated in vacuo to give 11.27 g (95%) of the title compound.

Workup

  1. customthe layers were separated
  2. washthe organic phase was washed with satd ag sodium bicarbonate (3×200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c03962031ef34e7a8baf52c5bfdf2470
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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