2-Fluoro-5-nitrobenzotrifluoride → 1-(Methylsulphonyl)-4-nitro-2-(trifluoromethyl)benzene

HRID 396799Notes

Reaction equation

HRID 396799 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][S:16]([O-:18])=[O:17].[Na+]>CS(C)=O>[CH3:15][S:16]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 2733271Sodium methanesulfinate

Product 1

HCID 206051531-(Methylsulphonyl)-4-nitro-2-(trifluoromethyl)benzeneYield 57.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-fluoro-5-nitrobenzotrifluoride (2.09 g, 10 mmol) and sodium methanesulfinate (1.32 g, 11 mmol) in DMSO (20 mL) was heated at 130° C. for 17.5 hours. After cooling down to room temperature, the mixture was poured into ice-water. The whole was extracted with ethyl acetate (30 mL×2), the combined organic layer washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was crystallized from hexane to give the subtitle compound (1.56 g, 57.8%, yield).

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionThe whole was extracted with ethyl acetate (30 mL×2)
  3. washthe combined organic layer washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-72ceefca634e4569a06b77505b891b93
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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