Acetone → 2-Fluoro-5-methanesulfonyl-benzoic acid

HRID 1934713Notes

Reaction equation

HRID 1934713 reaction equation
S([O-])([O-])=O.[Na+].[Na+].Cl[S:8]([C:11]1[CH:12]=[CH:13][C:14]([F:20])=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17])(=[O:10])=[O:9].[CH3:21]C(C)=O>O.C(=O)([O-])[O-].[Na+].[Na+]>[F:20][C:14]1[CH:13]=[CH:12][C:11]([S:8]([CH3:21])(=[O:10])=[O:9])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 6089842-Fluoro-5-chlorosulfonylbenzoic acid

Product 1

HCID 224675662-Fluoro-5-methanesulfonyl-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium sulphite (10.6 g) in water (20 mL) was warmed to 80° C. and slowly added with stirring to a solution of 5-chlorosulfonyl-2-fluorobenzoic acid (10 g) in acetone (10 mL), saturated aqueous sodium carbonate being added simultaneously for keeping the liquid in alkaline. The mixture was stirred at 60° C. for one and a half hours, and concentrated in vacuo. The residue was suspended in a mixture of ethanol (20 mL) and water (20 mL), then iodomethane (2.61 mL) was added to the mixture. The reaction mixture was stirred for 2 hours at 60° C. and for an hour at 100° C. After cooling to ambient temperature, ethanol was removed in vacuo. The resultant aqueous solution was acidified with concentrated hydrochloric acid. The aqueous solution was extracted with chloroform (3 times), and the combined organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residual oil was crystallized from ethanol to give 2-fluoro-5-methanesulfonylbenzoic acid (563.6 mg) as a colorless solid.

Workup

  1. additionslowly added
  2. additionadded simultaneously
  3. concentrationconcentrated in vacuo
  4. additionThe residue was suspended in a mixture of ethanol (20 mL) and water (20 mL)
  5. additioniodomethane (2.61 mL) was added to the mixture
  6. stirringThe reaction mixture was stirred for 2 hours at 60° C. and for an hour at 100° C
  7. temperatureAfter cooling to ambient temperature
  8. customethanol was removed in vacuo
  9. extractionThe aqueous solution was extracted with chloroform (3 times)
  10. dry with materialthe combined organic layer was dried over magnesium sulfate
  11. customAfter evaporation of the solvent
  12. customthe residual oil was crystallized from ethanol

Sources & evidence

ORD record
ord-04f9da3fbed9413784c8fbd1a775d643
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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