Hydrogen iodide → 2,6-Dibromoanthracene

HRID 506211Notes

Reaction equation

HRID 506211 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 then cooled to room temperature and poured into ice water (800 mL). Thereafter, the precipitate was filtered and washed with water and ethanol. The precipitate was then re-crystallized from toluene (620 mL) to give 14.49 g of pale yellow flake-like crystals of 2,6-dibromoanthracene (Compound 24).

Workup

  1. temperaturewas refluxed for 5 days
  2. filtrationThereafter, the precipitate was filtered
  3. washwashed with water and ethanol
  4. customThe precipitate was then re-crystallized from toluene (620 mL)

Sources & evidence

ORD record
ord-9506387026d14b449bb4a3e21156d892
Source dataset
uspto-grants-2010_08
Patent number
US07781761B2

Reaction notes

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