Sodium Hydroxide → 2-Bromo-5-methylbenzenesulfinic acid

HRID 842317Notes

Reaction equation

HRID 842317 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[S:15](Cl)(=[O:17])=[O:16].[OH-].[Na+]>O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[S:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 151553382-Bromo-5-methylbenzene-1-sulfonyl chloride

Product 1

HCID 151553372-Bromo-5-methylbenzenesulfinic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

37.6 g of sodium sulfite are dissolved in 500 ml of water and heated to 70° C. 62 g of 2-bromo-5-methylbenzenesulfonyl chloride are added in portions at this temperature. A 10 N aqueous NaOH solution is simultaneously added dropwise here so that the pH of the solution is kept between pH=9 and pH=10. The mixture is stirred at 70° C. for 1.5 hours, and the solution is filtered off and subsequently adjusted to pH=0 in an ice bath using a saturated aqeuous HCl solution. The mixture is stirred for 30 minutes, then the product is filtered off, subsequently washed with a little water and dried. 49.6 g of white crystals are obtained,

Workup

  1. filtrationthe solution is filtered off
  2. customsubsequently adjusted to pH=0 in an ice bath
  3. stirringThe mixture is stirred for 30 minutes
  4. filtrationthe product is filtered off
  5. washsubsequently washed with a little water
  6. customdried

Sources & evidence

ORD record
ord-d9fee858fa0d4a1ebb22ffce121df23c
Source dataset
uspto-grants-2002_04
Patent number
US06372917B1

Reaction notes

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