Benzene → HCID 23154691, compound

HRID 1913845Notes

Reaction equation

HRID 1913845 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>O.[N+](C)([O-])=O>[C:13]1([S:9]([C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:11])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23154691HCID 23154691, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6375NitromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A modification of the published procedures of Hagberg, Olson, and Sheares in Macromolecules, 2004, 37, 4748 was used. A 200 mL round-bottom flask equipped with a reflux condenser, stirring bar, and gas inlet was charged with 2,5-dichlorobenzenesulfonyl chloride (12.28 g, 50 mmoles), benzene (13.4 mL, 150 mmoles), and anhydrous nitromethane (50 mL). Aluminum chloride (7.33 g, 55 mmoles) was added and the mixture stirred until dissolved under nitrogen. The solution was heated to 100° C. overnight. The solution was cooled to room temperature and poured into 100 g water mixed with 25 mL hydrochloric acid. The mixture was extracted several times with dichloromethane. The organic extracts were dried with sodium sulfate, filtered, and evaporated, then the solids were dried in a vacuum oven to give 14.38 g (100% crude yield). The solids were recrystallized from ethanol after treating with decolorizing carbon to give about 14 g in two crops. The solids were recrystallized from ethanol to give 12.24 g (85% yield) of 2-benzenesulfonyl-1,4-dichlorobenzene. 1H NMR (DMSO-d6): 7.65 (ddd, 8.4, 7.5, 1.7 Hz, 2H), 7.67 (d, 8.6 Hz, 1H), 7.76 (tt, 7.5, 1.2 Hz, 1H), 7.83 (dd, 8.6, 2.6 Hz, 1H), 7.98 (ddd, 8.4, 1.7, 1.2 Hz, 2H), 8.27 (d, 2.6 Hz, 1H).

Workup

  1. customA 200 mL round-bottom flask equipped with a reflux condenser
  2. stirringthe mixture stirred
  3. dissolutionuntil dissolved under nitrogen
  4. temperatureThe solution was cooled to room temperature
  5. extractionThe mixture was extracted several times with dichloromethane
  6. dry with materialThe organic extracts were dried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customthe solids were dried in a vacuum oven
  10. customto give 14.38 g (100% crude yield)
  11. customThe solids were recrystallized from ethanol
  12. additionafter treating with decolorizing carbon
  13. customto give about 14 g in two crops
  14. customThe solids were recrystallized from ethanol

Sources & evidence

ORD record
ord-648f83f464dd4388b8397a1046986c92
Source dataset
uspto-grants-2013_12
Patent number
US08609804B2

Reaction notes

Loading…