3,4-Difluorobenzaldehyde → 3-Fluoro-4-methanesulfonylbenzaldehyde

HRID 908198Notes

Reaction equation

HRID 908198 reaction equation
[Na+].[CH3:2][S:3]([O-:5])=[O:4].[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1F)[CH:10]=[O:11]>CS(C)=O>[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[S:3]([CH3:2])(=[O:5])=[O:4])[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 5880883,4-DifluorobenzaldehydeHCID 2733271Sodium methanesulfinate

Product 1

HCID 212517323-Fluoro-4-methanesulfonylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
67.5 °C

Procedure

Methane sulfinic acid sodium salt (22.65 g, 220 mmol) is added to a stirred solution of 3,4-difluorobenzaldehyde (25 g, 175 mmol) in dry DMSO (200 ml). The mixture is heated at 65-70° C. for 5 hours then poured onto ice-water (500 ml). The precipitate is filtered, washed with water and dissolved in chloroform (400 ml). The organic extract is washed with water (2×200 ml), dried over MgSO4, filtered and concentrated to give the titled compound as a white solid.

Workup

  1. additionthen poured onto ice-water (500 ml)
  2. filtrationThe precipitate is filtered
  3. washwashed with water
  4. dissolutiondissolved in chloroform (400 ml)
  5. extractionThe organic extract
  6. washis washed with water (2×200 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9f8e00289767472aa4b5f95bbb0cb9b7
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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