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

HRID 888684Notes

Reaction equation

HRID 888684 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>C1(C)C=CC=CC=1.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

7

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 73.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Approximately 7.6 g (17 mmol) of the obtained 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol, 5.1 g (31 mmol) of potassium iodide, 9.7 g (92 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 refluxed at 120° C. for 2 hours. Then, 30 mL of 50% phosphinic acid was added to the reactive mixture, and the mixture was stirred for 1 hour at 120° C. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were dried with magnesium sulfate, filtered by suction filtration and the obtained filtrate was concentrated to obtain a solid substance. The solid substance was dissolved in toluene, and the solution was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina. The obtained filtrate was concentrated to obtain a solid substance, and the solid substance was recrystallized with a mixed solvent of chloroform and hexane, giving 5.1 g of 2-bromo-9,10-diphenylanthracene as a light yellow powdered solid substance which was the object of the synthesis. The yield of the two stages (ii) and (iii) was 74%.

Workup

  1. customAfter the reaction
  2. washthe solution was washed with water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe extracted solution and an organic layer were dried with magnesium sulfate
  5. filtrationfiltered by suction filtration
  6. concentrationthe obtained filtrate was concentrated
  7. customto obtain a solid substance
  8. filtrationthe solution was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina
  9. concentrationThe obtained filtrate was concentrated
  10. customto obtain a solid substance
  11. customthe solid substance was recrystallized with a mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-5153a1525fc140f8bdb7ce7a57253674
Source dataset
uspto-grants-2012_08
Patent number
US08251765B2

Reaction notes

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