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

HRID 497197Notes

Reaction equation

HRID 497197 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-2b2bae256fe0489abc6e9296392b5477
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

Loading…