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

HRID 1754505Notes

Reaction equation

HRID 1754505 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

Procedure

Methane sulfinic acid sodium salt (20.1 g, 200 mmol) is added to a stirred solution of 3,4-difluorobenzaldehyde (22.5 g, 158 mmol) in dry DMSO (200 ml) at 75° C. After 2 hours the reaction is poured onto ice-water (200 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 and the solvent is removed in vacuo to give the titled compound as a white solid.

Workup

  1. additionAfter 2 hours the reaction is poured onto ice-water (200 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. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-36a549e60e62439dac0a49c4e2f3a44b
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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