Sodium Sulfite → Sodium 4-bromo-3-methylbenzenesulfinate

HRID 1972688Notes

Reaction equation

HRID 1972688 reaction equation
C(=O)(O)[O-].[Na+:5].S([O-])([O-])=O.[Na+].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][C:14]=1[CH3:23]>O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O-:21])=[O:20])=[CH:15][C:14]=1[CH3:23].[Na+:5]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27375034-Bromo-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 23712900Sodium 4-bromo-3-methylbenzenesulfinateYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 100-mL round-bottomed flask was added sodium bicarbonate (1.18 g, 14 mmol, Sigma-Aldrich, St. Louis, Mo.), sodium sulfite (1.77 g, 14 mmol, Sigma-Aldrich, St. Louis, Mo.) and water (15 mL). The reaction mixture was heated at 80° C. and 4-bromo-3-methylbenzenesulfonyl chloride (3.15 g, 11.69 mmol, Sigma-Aldrich, St. Louis, Mo.) was added portion-wise. When the addition was completed the reaction mixture was heated at 90° C. for 3 h and allowed to cool to room temperature. The solvent was partially removed under vacuum and the white precipitate obtained was filtered and dried in vacuo to provide sodium 4-bromo-3-methylbenzenesulfinate (2.94 g) that was used without further purification.

Workup

  1. additionWhen the addition
  2. temperaturewas heated at 90° C. for 3 h
  3. temperatureto cool to room temperature
  4. customThe solvent was partially removed under vacuum
  5. customthe white precipitate obtained
  6. filtrationwas filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5b81871b0c894ceab2887c692422140f
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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