Benzene → HCID 66627755, compound

HRID 1913844Notes

Reaction equation

HRID 1913844 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:19](Cl)(=[O:21])=[O:20])[C:5]([C:8]2[C:9]([S:15](Cl)(=[O:17])=[O:16])=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>[N+](C)([O-])=O>[C:27]1([S:19]([C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=2[C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[S:15]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:17])=[O:16])(=[O:21])=[O:20])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 86660797HCID 86660797, compound

Product 1

HCID 66627755HCID 66627755, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Inside a glove box, a 125 mL round-bottom flask equipped with a stirring bar, reflux condenser, and gas inlet was charged with 4,4′-dibromobiphenyl-2,2′-disulfonyl dichloride (10.18 g, 20 mmoles) and aluminum chloride (5.87 g, 44 mmoles). Benzene (14 mL) and anhydrous nitromethane (40 mL) were added and the mixture stirred until dissolved. The solution was heated to 100° C. for about 8 hours. The solution was cooled to room temperature and poured onto 200 g ice mixed with 100 mL hydrochloric acid. The mixture was extracted several times with dichloromethane. The organic extracts were washed twice with water, dried with sodium carbonate, filtered, and evaporated to give 11.75 g (99%). The mixture was purified by column chromatography using silica gel and dichloromethane (Rf 0.32) to give 8.73 g (74% yield) of 2,2′-bis-benzenesulfonyl-4,4′-dibromobiphenyl.

Workup

  1. customInside a glove box, a 125 mL round-bottom flask equipped with a stirring bar
  2. temperaturereflux condenser, and gas inlet
  3. dissolutionuntil dissolved
  4. temperatureThe solution was cooled to room temperature
  5. extractionThe mixture was extracted several times with dichloromethane
  6. washThe organic extracts were washed twice with water
  7. dry with materialdried with sodium carbonate
  8. filtrationfiltered
  9. customevaporated
  10. customto give 11.75 g (99%)
  11. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-ec979f12f106474cbc84f198549fe43b
Source dataset
uspto-grants-2013_12
Patent number
US08609804B2

Reaction notes

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