Potassium Iodide → HCID 58184754, compound

HRID 1177828Notes

Reaction equation

HRID 1177828 reaction equation
[Br:1][C:2]1[C:15]2[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[I-].[K+].O.[PH2](=O)[O-].[Na+].[PH2](=O)O>C(O)(=O)C>[Br:1][C:2]1[C:15]2[C:6](=[C:7]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:8]3[C:13]([C:14]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 4124402Phosphinic AcidHCID 66702141HCID 66702141, compoundHCID 178418950HCID 178418950, compound

Product 1

HCID 58184754HCID 58184754, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

14.4 g (32.4 mmol) of 1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol, 9.68 g (58.3 mmol) of potassium iodide, 18.6 g (175 mmol) of sodium phosphinate monohydrate, and 100 mL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was refluxed for 5 hours at 120° C. After the reaction was completed, 40 mL of a 50% phosphinic acid was added to the mixture, and stirring was kept for 18 hours at room temperature. After the reaction was completed, the reaction solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted part was combined with the organic layer, and then dried with magnesium sulfate. After drying, a mixture was subjected to suction filtration, and the filtrate was concentrated. The obtained residue was dissolved in toluene, and filtered through Florisil, celite, and then alumina, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (eluent; toluene:hexane=1:5). The resulting solid was washed with ethanol, providing 0.50 g of 1-bromo-9,10-diphenylanthracene as light yellow powder in 3.8% yield.

Workup

  1. washthe reaction solution was washed with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. customAfter drying
  5. filtrationa mixture was subjected to suction filtration
  6. concentrationthe filtrate was concentrated
  7. dissolutionThe obtained residue was dissolved in toluene
  8. filtrationfiltered through Florisil, celite
  9. concentrationalumina, and the filtrate was concentrated
  10. customThe obtained residue was purified by silica gel column chromatography (eluent; toluene:hexane=1:5)
  11. washThe resulting solid was washed with ethanol

Sources & evidence

ORD record
ord-37bd9b2e03a643a8bd963fe93c9dc0e0
Source dataset
uspto-grants-2010_11
Patent number
US07842945B2

Reaction notes

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