Sulfuric Acid → HCID 66783297, compound

HRID 1096575Notes

Reaction equation

HRID 1096575 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][C:12]=1[I:13].[CH2:14]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].ClCC(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O>>[Br:1][C:2]1[C:12]([I:13])=[CH:11][C:5]2[C:6](=[O:8])[C:30]3[C:29](=[CH:28][C:27]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[C:26]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:31]=3)[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 124181,1,1,2-TetrachloroethaneHCID 1135411,2-DidodecylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 86635070HCID 86635070, compound

Product 1

HCID 66783297HCID 66783297, compoundYield 35%

Procedure

To a 100 ml three-necked flask were added 1.00 g (2.83=mol) of 4-bromo-5-iodophthalic anhydride synthesized in the above, 1.29 g (3.11 mmol) of 1,2-didodecylbenzene, and 4 ml of tetrachloroethane. Thereto was added 0.82 g (6.15 mmol) of aluminum chloride, followed by 3 hours of stirring at room temperature. Ice was added portionwise to the resulting reaction mixture to quench the reaction, followed by extraction with toluene. The extract was concentrated under reduced pressure to obtain 2.5 g of a viscous matter. To the viscous matter was added 8 ml of sulfuric acid, followed by 2 hours of stirring at 80° C. The resulting reaction mixture was cooled to room temperature and ice was added. The mixture was extracted with toluene and the organic phase was dried over sodium sulfate. Then, the phase was filtrated and concentrated under reduced pressure to obtain 678 mg of 2-bromo-3-iodo-6,7-didodecylanthraquinone (yield 35%).

Workup

  1. additionIce was added portionwise to the resulting reaction mixture
  2. customto quench
  3. customthe reaction
  4. extractionfollowed by extraction with toluene
  5. concentrationThe extract was concentrated under reduced pressure
  6. customto obtain 2.5 g of a viscous matter
  7. waitfollowed by 2 hours
  8. stirringof stirring at 80° C
  9. customThe resulting reaction mixture
  10. temperaturewas cooled to room temperature
  11. additionice was added
  12. extractionThe mixture was extracted with toluene
  13. dry with materialthe organic phase was dried over sodium sulfate
  14. filtrationThen, the phase was filtrated
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75a0c8f0f0744f89b1baa94f0d14b988
Source dataset
uspto-grants-2012_03
Patent number
US08138355B2

Reaction notes

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