1,2-Difluoro-4-nitrobenzene → 2-Fluoro-1-(methylsulfonyl)-4-nitrobenzene

HRID 2086654Notes

Reaction equation

HRID 2086654 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][S:13]([O-:15])=[O:14].[Na+]>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[S:13]([CH3:12])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 1230531,2-Difluoro-4-nitrobenzeneHCID 2733271Sodium methanesulfinate

Product 1

HCID 223167812-Fluoro-1-(methylsulfonyl)-4-nitrobenzeneYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3,4-difluoronitrobenzene (10 g, 62.9 mmol) and sodium methanesulfinate (8.3 g, 69.1 mmol) in DMSO (60 mL) was heated at 130° C. for 8 hours. After cooling down to room temperature, the mixture was poured into ice-water. The whole was extracted with ethyl acetate (200 mL×2), the combined organic layer washed with water (80 mL), brine (80 mL), dried over MgSO4, and concentrated in vacuo. The residue was crystallized from hexane and triturated with hexane to give the subtitle compound (10.2 g, 74% yield).

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionThe whole was extracted with ethyl acetate (200 mL×2)
  3. washthe combined organic layer washed with water (80 mL), brine (80 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from hexane
  7. customtriturated with hexane

Sources & evidence

ORD record
ord-a21045baead74134ad358444a19f8ef2
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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