Potassium Iodide → 2-Bromo-9,10-bis(4-fluorophenyl)anthracene

HRID 1640225Notes

Reaction equation

HRID 1640225 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)(O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=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:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:6]3[C:11]([C:12]=2[C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 4124402Phosphinic AcidHCID 592111502-Bromo-9,10-bis(4-fluorophenyl)-9,10-dihydro-9,10-anthracenediolHCID 178418950HCID 178418950, compound

Product 1

HCID 592111052-Bromo-9,10-bis(4-fluorophenyl)anthraceneYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

8.32 (17.3 mmol) of 2-bromo-9,10-bis(4-fluorophenyl)-9,10-dihydro-9,10-anthracenediol, 5.17 g (31.1 mmol) of potassium iodide, 9.90 g (93.4 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 200 mL three-neck flask, and the mixture was refluxed at 120° C. for 4 hours. Then, 20 mL of a 50% phosphinic acid was added into the reaction mixture, and the mixture was stirred for 1 hour at 120° C. After the reaction, the reaction mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. This extracted solution was combined with the organic layer, and then dried with magnesium sulfate. After drying, the 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 recrystallized with chloroform and hexane, giving 7.2 g of 2-bromo-9,10-bis(4-fluorophenyl)anthracene as light yellow powder in 74% yield.

Workup

  1. customAfter the reaction
  2. washthe reaction mixture was washed with water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. customAfter drying
  6. filtrationthe mixture was subjected to suction filtration
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe obtained residue was dissolved in toluene
  9. filtrationfiltered through Florisil, celite
  10. concentrationalumina, and the filtrate was concentrated
  11. customThe obtained residue was recrystallized with chloroform and hexane

Sources & evidence

ORD record
ord-f68b97c1f4f9458bb5be0965f76fc71d
Source dataset
uspto-grants-2012_02
Patent number
US08110980B2

Reaction notes

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