Potassium Iodide → HCID 59561159, compound

HRID 926678Notes

Reaction equation

HRID 926678 reaction equation
[CH3:1][C:2]1([CH3:47])[C:14]2[CH:13]=[C:12]([C:15]3(O)[C:28]4[CH:27]=[C:26]([Br:29])[CH:25]=[CH:24][C:23]=4[C:22]([C:31]4[CH:43]=[CH:42][C:41]5[C:40]6[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=6)[C:34]([CH3:45])([CH3:44])[C:33]=5[CH:32]=4)(O)[C:21]4[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.O.[PH2](=O)[O-].[Na+].[I-].[K+].[PH2](=O)O>C(O)(=O)C.O>[CH3:1][C:2]1([CH3:47])[C:14]2[CH:13]=[C:12]([C:15]3[C:16]4[C:21]([C:22]([C:31]5[CH:43]=[CH:42][C:41]6[C:40]7[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=7)[C:34]([CH3:45])([CH3:44])[C:33]=6[CH:32]=5)=[C:23]5[C:28]=3[CH:27]=[C:26]([Br:29])[CH:25]=[CH:24]5)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 4124402Phosphinic AcidHCID 59561152HCID 59561152, compoundHCID 178418950HCID 178418950, compound

Product 1

HCID 59561159HCID 59561159, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 46 mmol of 9,10-bis(9,9-dimethylfluorene-2-yl)-2-bromo-9,10-dihydroanthracene-9,10-diol, 24 g (0.23 mol) of sodium phosphinate monohydrate, and 15 g (91 mmol) of potassium iodide in 100 mL of glacial acetic acid was stirred for 4 hours at 120° C. After the reaction, 60 mL of a 50% phosphinic acid was added to the reaction mixture, and then stirring was kept for additional 2 hours at 120° C. Water was added to the mixture, and the mixture was stirred for 1 hour. After the mixture was filtered, the resulting solid was washed with water and dissolved in toluene, and the toluene-solution was washed with a saturated sodium bicarbonate aqueous solution and brine. Magnesium sulfate was added to this organic layer to dry the organic layer. This mixture was subjected to suction filtration, and the filtrate was filtered through celite, Florisil, and then alumina. The filtrate was concentrated, and the resulting solid was dissolved in a mixed solvent of chloroform and methanol, which was followed by irradiating ultrasound to yield 14 g of the title compound as a light yellow solid. Total yield of the steps of (ii) and (iii) was 47%.

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe mixture was stirred for 1 hour
  3. filtrationAfter the mixture was filtered
  4. washthe resulting solid was washed with water
  5. dissolutiondissolved in toluene
  6. washthe toluene-solution was washed with a saturated sodium bicarbonate aqueous solution and brine
  7. additionMagnesium sulfate was added to this organic layer
  8. customto dry the organic layer
  9. filtrationThis mixture was subjected to suction filtration
  10. filtrationthe filtrate was filtered through celite, Florisil
  11. concentrationThe filtrate was concentrated
  12. dissolutionthe resulting solid was dissolved in a mixed solvent of chloroform and methanol, which
  13. customby irradiating ultrasound

Sources & evidence

ORD record
ord-8cdb1fd92e9a4e87907fa48a9280fb3d
Source dataset
uspto-grants-2016_03
Patent number
US09287511B2

Reaction notes

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