Sodium Sulfite → Sodium 4-bromo-3-methylbenzenesulfinate

HRID 2376988Notes

Reaction equation

HRID 2376988 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12].S([O-])([O-])=O.[Na+:17].[Na+].C(=O)([O-])O.[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:12].[Na+:17]

Participants

5

Reactant 3

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

Product 1

HCID 23712900Sodium 4-bromo-3-methylbenzenesulfinateYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-Bromo-3-methylbenzenesulfonyl chloride (1.145 g, 4.25 mmol) was added portion wise to a solution of sodium sulfite (0.578 g, 2.29 mmol) and sodium hydrogen carbonate (0.749 g, 2.4 mmol) in water (10 mL) at 80° C. The reaction was heated to 90° C. for 3 h. The cooled reaction mixture was evaporated in vacuo to half-volume, at which point a precipitate appeared. This was removed by filtration. The filtrate was concentrated further then cooled to 5° C. and the precipitate removed by filtration. The combined residues were washed with water and dried to give sodium 4-bromo-3-methylbenzenesulfinate (0.54 g).

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated in vacuo to half-volume, at which point a precipitate
  3. customThis was removed by filtration
  4. concentrationThe filtrate was concentrated further
  5. temperaturethen cooled to 5° C.
  6. customthe precipitate removed by filtration
  7. washThe combined residues were washed with water
  8. customdried

Sources & evidence

ORD record
ord-0e084f5df506491896064bcb76f9a806
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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