Potassium Iodide → 2-Bromo-9,10-diphenylanthracene

HRID 926668Notes

Reaction equation

HRID 926668 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(O)[C:4]=2[CH:3]=1.[I-].[K+].O.[PH2](=O)[O-].[Na+].[PH2](=O)O>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:6]3[C:11]([C:12]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 4124402Phosphinic AcidHCID 231602182-Bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diolHCID 178418950HCID 178418950, compound

Product 1

HCID 222471632-Bromo-9,10-diphenylanthraceneYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

7.55 g (16.95 mmol) of the obtained 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol, 5.06 g (30.51 mmol) of potassium iodide, 9.70 g (91.52 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was heated at 120° C. for 2 hours. Thereafter, 30 mL of 50% phosphinic acid was added to the mixture, and the mixture was stirred for 1 hour at 120° C. After the reaction, the mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in toluene, and the solution was filtered through celite, and then alumina. The filtrate was concentrated, and the residue was recrystallized with chloroform and hexane, giving 5.1 g of 2-bromo-9,10-diphenylanthracene as a light yellow solid in 74% yield.

Workup

  1. customAfter the reaction
  2. washthe mixture was washed with water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in toluene
  8. filtrationthe solution was filtered through celite
  9. concentrationThe filtrate was concentrated
  10. customthe residue was recrystallized with chloroform and hexane

Sources & evidence

ORD record
ord-a505e99d80fa4f69b12487f5da89e32d
Source dataset
uspto-grants-2016_03
Patent number
US09287511B2

Reaction notes

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