Dimethyl Sulfoxide → 3-Bromo-4-(methanesulfonyl)benzaldehyde

HRID 1532276Notes

Reaction equation

HRID 1532276 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].CS(C)=O.[Na+].[CH3:16][S:17]([O-:19])=[O:18]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:17]([CH3:16])(=[O:19])=[O:18])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 2733271Sodium methanesulfinate

Product 1

HCID 212517343-Bromo-4-(methanesulfonyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution containing 0.5 g 3-bromo-4-fluorobenzaldehyde and 20 ml of DMSO was added 0.49 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 extract with ethyl acetate. The extract was evaporated to dryness in vacuo. The residue was triturated with 2-propanol, yield 0.69 g. 1H-NMR (DMSO-d6, 400 MHz): 3.52 (s, 3 H, CH3), 8.10-8.47 (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 extract with ethyl acetate
  4. customThe extract was evaporated to dryness in vacuo
  5. customThe residue was triturated with 2-propanol, yield 0.69 g

Sources & evidence

ORD record
ord-6905448a5bc04a3fb415290c2d180c71
Source dataset
uspto-grants-2001_03
Patent number
US06201027B1

Reaction notes

Loading…