o-Fluorobenzaldehyde → 2-Tosylbenzaldehyde

HRID 1795115Notes

Reaction equation

HRID 1795115 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Na+].[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([S:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>CS(C)=O>[CH3:20][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 67970o-FluorobenzaldehydeHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 8943612-TosylbenzaldehydeYield 39%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-fluorobenzaldehyde (12.4 g, 100 mmol) in DMSO (75 mL) is added p-toluenesulfinic acid sodium salt (19.6 g, 110 mmol), and the reaction mixture is heated to 100° C. for 16 h. Once complete, the reaction mixture is cooled to room temperature and poured onto ice. The product is then isolated as a white solid by filtration to afford 2-[(4-methylphenyl)sulfonyl]benzaldehyde (10.1 g, 39%).

Workup

  1. temperatureOnce complete, the reaction mixture is cooled to room temperature
  2. additionpoured onto ice
  3. customThe product is then isolated as a white solid by filtration

Sources & evidence

ORD record
ord-833b01d3a38544e5bc981d33251a1741
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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