4-Fluoro-3-(trifluoromethyl)benzaldehyde → 4-Methanesulfonyl-3-trifluoromethyl-benzaldehyde

HRID 908190Notes

Reaction equation

HRID 908190 reaction equation
[Na+].[CH3:2][S:3]([O-:5])=[O:4].F[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[C:15]([F:18])([F:17])[F:16]>CS(C)=O>[CH3:2][S:3]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[C:15]([F:16])([F:18])[F:17])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehydeHCID 2733271Sodium methanesulfinate

Product 1

HCID 714799064-Methanesulfonyl-3-trifluoromethyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

Methane sulfinic acid sodium salt (6.65 g, 65.1 mmol) is added to a stirred solution of 4-Fluoro-3-trifluoromethyl-benzaldehyde (10.0 g, 52.1 mmol) in dry DMSO (200 ml) and the mixture is heated at 75° C. After 2 hours the reaction is allowed to cool and poured onto ice-water (300 ml). The precipitate is collected by filtration, washed with water and dissolved in dichloromethane (200 ml). The organic extract is washed with water (3×200 ml), dried over MgSO4, filtered, and the solvent is removed to give the title compound as a white solid.

Workup

  1. temperatureto cool
  2. additionpoured onto ice-water (300 ml)
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in dichloromethane (200 ml)
  6. extractionThe organic extract
  7. washis washed with water (3×200 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthe solvent is removed

Sources & evidence

ORD record
ord-a01b87c1ceeb45f79b05a16b703e4ad5
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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