Acetic Acid → 4-Chloro-3-fluoro-2-methylsulphonylbenzoic acid

HRID 1491585Notes

Reaction equation

HRID 1491585 reaction equation
OO.[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6](SC)[C:5]=1[F:15].[S:16](=[O:20])(=O)(O)[OH:17].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[C:30](O)(=O)C>>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([S:16]([CH3:30])(=[O:20])=[O:17])[C:5]=1[F:15]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 656671Sodium PyrosulfiteHCID 152187374-Chloro-3-fluoro-2-methylsulphenylbenzoic acid

Product 1

HCID 544424304-Chloro-3-fluoro-2-methylsulphonylbenzoic acid

Conditions

Temperature
80 °C

Procedure

Hydrogen peroxide (30%; 66 ml) was added to a suspension of 4-chloro-3-fluoro-2-(methylsulphenyl)benzoic acid (2.5 g) and concentrated sulphuric acid (1.5 ml) in acetic acid. The mixture was heated slowly to 80° C. and stirred and heated at that temperature overnight. It was cooled to room temperature and treated with sodium metabisulphite (45 g). It was evaporated and the residue was treated with water and acidified to pH 1. It was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 4-chloro-3-fluoro-2-methylsulphonylbenzoic acid (24 g) as an off white solid m.p. 196°-200° C.

Workup

  1. temperatureheated at that temperature overnight
  2. temperatureIt was cooled to room temperature
  3. customIt was evaporated
  4. additionthe residue was treated with water
  5. extractionIt was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-0c8b08f3d48c42778baea2591b7f3287
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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