4-Fluorobenzaldehyde → 4-(Benzenesulfonyl)benzaldehyde

HRID 1644697Notes

Reaction equation

HRID 1644697 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[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][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 144174774-(Benzenesulfonyl)benzaldehydeYield 378.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluorobenzaldehyde (6 g, 48 mmol), sodium benzenesulfinate (7.5 g, 4.6 mmol), and dimethylsulfoxide (30 mL) was heated at 100° C. for 20 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. A solution of this crude product and dichloromethane was evaporated over silica gel, and the resulting silica gel supported crude product was purified using flash chromatography (Analogix SuperFlash™ column, 15%-40% ethyl acetate in hexanes) to give 4.29 g (41%) of 4-(benzenesulfonyl)-benzaldehyde as a white solid.

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. customA solution of this crude product and dichloromethane was evaporated over silica gel
  8. customwas purified

Sources & evidence

ORD record
ord-c889a03c32e147cc9b8475e2350cff81
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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