Hydrochloric Acid → 4-Chloro-2-nitrobenzene-1-sulfonic acid

HRID 513716Notes

Reaction equation

HRID 513716 reaction equation
[O-:1][S:2]([O-:4])=[O:3].[Na+].[Na+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11](F)=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1.Cl>CCO.O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:2]([OH:4])(=[O:1])=[O:3])=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 676604-Chloro-1-fluoro-2-nitrobenzene

Product 1

HCID 4268414-Chloro-2-nitrobenzene-1-sulfonic acidYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of Na2SO3 (3.26 g, 25.9 mmol) in EtOH (32 ml) and water (40 ml) was added to a solution of 5-chloro-2-fluoro nitrobenzene (2.0 g, 11.4 mmol) in EtOH (24 ml) and the mixture was heated at 70° C. for 16 h. After cooling, the mixture was acidified to pH=2 with conc. HCl (2 ml) and the solvent was removed in vacuo. The residue was diluted with brine solution (12 ml) and the mixture was heated under reflux for 2 h. The solution was cooled in ice bath and the resulting precipitate was collected by filtration to give the title compound (1.54 g, 57%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. additionThe residue was diluted with brine solution (12 ml)
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 2 h
  6. temperatureThe solution was cooled in ice bath
  7. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-471eb071a869493789e75f0bfd86a948
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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