Sodium Iodide → HCID 11132285, compound

HRID 1844620Notes

Reaction equation

HRID 1844620 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+].[I-:27].[Na+]>CC(=O)CC>[I:27][CH2:17][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 143474-Hydroxybenzophenone

Product 1

HCID 11132285HCID 11132285, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

A 1000 mL three-neck flask was charged with 4-hydroxybenzophenone (50.00 g; 252.2 mmol), 1-bromo-3-chloropropane (79.41 g; 504.4 mmol) and 2-butanone (500 mL). After flushing with nitrogen, anhydrous potassium carbonate (104.6 g; 756.5 mmol) was added and the reaction mixture was stirred at reflux for 24 h. Full consumption of the starting 4-hydroxybenzophenone was confirmed by TLC. The reaction mixture was filtered, the filtrate evaporated, the oily residue dissolved in dichloromethane (300 mL) and extracted with water (3×100 mL). The organic phase was separated, evaporated, and the unreacted 1-bromo-3-chloropropane was removed by heating to 70° C. in vacuo. The residue was dissolved in 2-butanone (500 mL) and sodium iodide (45.36 g; 302.6 mmol) was added. The reaction mixture was refluxed for 6 h. The reaction mixture was filtered, the filtrate evaporated, the oily residue dissolved in dichloromethane (300 mL) and extracted with water (3×100 mL). The organic phase was separated, evaporated, the light brown oily residue dried in vacuo to give crude 4-(3-iodopropoxy)benzophenone (light brown solid; 83.2 g).

Workup

  1. additionwas added
  2. temperatureat reflux for 24 h
  3. customconsumption of the starting 4-hydroxybenzophenone
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated
  6. dissolutionthe oily residue dissolved in dichloromethane (300 mL)
  7. extractionextracted with water (3×100 mL)
  8. customThe organic phase was separated
  9. customevaporated
  10. customthe unreacted 1-bromo-3-chloropropane was removed
  11. dissolutionThe residue was dissolved in 2-butanone (500 mL)
  12. temperatureThe reaction mixture was refluxed for 6 h
  13. filtrationThe reaction mixture was filtered
  14. customthe filtrate evaporated
  15. dissolutionthe oily residue dissolved in dichloromethane (300 mL)
  16. extractionextracted with water (3×100 mL)
  17. customThe organic phase was separated
  18. customevaporated
  19. customthe light brown oily residue dried in vacuo

Sources & evidence

ORD record
ord-a82155871ad74c77992b8e8b18d28ac9
Source dataset
uspto-grants-2015_02
Patent number
US08946449B2

Reaction notes

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