o-Fluorobenzaldehyde → 2-(phenylsulfonyl)benzaldehyde

HRID 1644700Notes

Reaction equation

HRID 1644700 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10]1([S:16]([O-:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Na+]>CS(C)=O>[C:10]1([S:16]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 67970o-Fluorobenzaldehyde2×HCID 2723840Benzenesulfinic acid, sodium salt2×

Product 1

HCID 6409162-(phenylsulfonyl)benzaldehydeYield 23%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
95 °C

Procedure

A mixture of 2-fluorobenzaldehyde (4.67 g, 37.6 mmol), sodium benzenesulfinate (6.79 g, 41.3 mmol), and dimethylsulfoxide (30 mL) was heated at 95° C. for 18 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated to give a white solid. NMR analysis of this crude mixture indicated unreacted 2-fluorobenzaldehyde to be the major component. The crude mixture was redissolved in dimethylsulfoxide (30 mL), then sodium benzenesulfinate (5.0 g, 30 mmol) was added. The resulting mixture was heated at 95° C. for another 16 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated. A solution of this crude product and dichloromethane was evaporated over silica gel, and the resulting silica gel supported crude product was loaded onto an Analogix SuperFlash™ column. Flash chromatography (5%-35% ethyl acetate in hexanes) provided 1.96 g (23%) of 2-(benzenesulfonyl)-benzaldehyde as a clear, colorless oil which partially solidified over time.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a white solid
  7. temperatureThe resulting mixture was heated at 95° C. for another 16 hours
  8. temperatureThe reaction mixture was cooled to room temperature
  9. custompartitioned between ethyl acetate and water
  10. dry with materialThe organic phase was dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customA solution of this crude product and dichloromethane was evaporated over silica gel

Sources & evidence

ORD record
ord-65c342be3b984124af46a3f99e38da6b
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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