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

HRID 396766Notes

Reaction equation

HRID 396766 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 withhexane 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 withhexane

Sources & evidence

ORD record
ord-9e813b661b60409e991a142e100f7ecc
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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