Dimethyl Sulfoxide → 3-Chloro-4-methanesulfonyl-benzaldehyde

HRID 1532274Notes

Reaction equation

HRID 1532274 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[Cl:10].CS(C)=O.[Na+].[CH3:16][S:17]([O-:19])=[O:18]>O>[Cl:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[S:17]([CH3:16])(=[O:19])=[O:18])[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5938663-Chloro-4-fluorobenzaldehydeHCID 2733271Sodium methanesulfinate

Product 1

HCID 117361153-Chloro-4-methanesulfonyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution containing 1.0 g 4-fluoro-3-chlorobenzaldehyde and 45 ml DMSO, was added 1.93 g methanesulfinic acid sodium salt with stirring at 90° C. The solution was stirred 6 hours at 90° C. and poured into water. Sodiumhydrogencarbonate was added and the product was extracted with ethyl acetate. The extract was evaporated to dryness in vacuo. The residue was triturated with 2-propanol, yield 1.06 g. 1H-NMR (DMSO-d6, 400 MHz): 3.45 (s, 3H, CH3), 8.09-8.27 (m, 3 H, Ar), 10.01 (d, 1 H, CHO).

Workup

  1. stirringThe solution was stirred 6 hours at 90° C.
  2. additionSodiumhydrogencarbonate was added
  3. extractionthe product was extracted with ethyl acetate
  4. customThe extract was evaporated to dryness in vacuo
  5. customThe residue was triturated with 2-propanol, yield 1.06 g

Sources & evidence

ORD record
ord-83d21be7db304f88a86ee19ac757fb32
Source dataset
uspto-grants-2001_03
Patent number
US06201027B1

Reaction notes

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