Hydrogen iodide → 2,6-Dibromoanthracene

HRID 491102Notes

Reaction equation

HRID 491102 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([Br:17])[CH:10]=3)[C:5](=O)[C:4]=2[CH:3]=1.I.[PH2](O)=O>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9]([Br:17])=[CH:8][CH:7]=3)[CH:3]=1

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 4124402Phosphinic AcidHCID 109594842,6-Dibromoanthraquinone

Product 1

HCID 220589062,6-Dibromoanthracene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Subsequently, a mixture of 2,6-dibromoanthraquinone (22.41 g, 61.23 mmol), acetic acid (250 mL), 56-58% hydriodic acid (100 mL), and 50% hypophosphorous acid (55 mL) was refluxed for 5 days. The mixture was cooled to RT and poured into ice water (800 mL). The resulting precipitate was filtered, washed with water and ethanol, and recrystallized from toluene (620 mL) to give 2,6-dibromoanthracene: 14.49 g pale yellow flake-like crystals.

Workup

  1. temperaturewas refluxed for 5 days
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water and ethanol
  4. customrecrystallized from toluene (620 mL)

Sources & evidence

ORD record
ord-03dfd762692b4b2c92cee5b15d9f63c1
Source dataset
uspto-grants-2009_05
Patent number
US07528448B2

Reaction notes

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