Sodium Sulfite → HCID 19875035, compound

HRID 465497Notes

Reaction equation

HRID 465497 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9](Cl)(=[O:11])=[O:10])=[CH:4][C:3]=1[CH3:13].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9]([OH:11])=[O:10])=[CH:4][C:3]=1[CH3:13]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 157253714-Fluoro-3,5-dimethylbenzenesulfonylchloride

Product 1

HCID 19875035HCID 19875035, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

4-Fluoro-3,5-dimethylbenzenesulphonyl chloride (5.56 g, 25 mmol) was added in portions to a solution of anhydrous sodium sulphite (6.0 g, 47.6 mmol) and sodium bicarbonate (4.2 g, 50 mmol) in water (25 ml) at 70° C. with vigorous stirring. When the addition was complete, the mixture was heated and stirred at 70° C. for a further 2 hours. The mixture was allowed to cool. The solid which crystallised from the solution was collected by filtration, dissolved in the minimum amount of water, and acidified to pH 1 with 2M hydrochloric acid. The resultant precipitate was extracted with ethyl acetate (3×75 ml) and the extracts were combined and dried (MgSO4). The solvent was evaporated. The solid residue was triturated with ether, collected by filtration, washed with ether and dried in vacuo to give 4-fluoro-3,5-dimethylbenzenesulphinic acid (4.7 g). This was converted directly to its sodium salt by addition to a solution of sodium methoxide (1 equivalent) in methanol and evaporation of the solution.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was heated
  3. temperatureto cool
  4. customThe solid which crystallised from the solution
  5. filtrationwas collected by filtration
  6. dissolutiondissolved in the minimum amount of water
  7. extractionThe resultant precipitate was extracted with ethyl acetate (3×75 ml)
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. customThe solid residue was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-9249de1c3013452ebbd4e342a57068e5
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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