Hydrogen iodide → 2,6-Dibromoanthracene

HRID 899940Notes

Reaction equation

HRID 899940 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-4dcb0c00c15746dbb4d33201dd9aa6ec
Source dataset
uspto-grants-2008_04
Patent number
US07355199B2

Reaction notes

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