Potassium Iodide → (4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

HRID 132990Notes

Reaction equation

HRID 132990 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].FC(F)(F)C([O-])=O.[Tl+].[I-:30].[K+].C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[C:9]([I:30])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 21902506Thallium(1+);2,2,2-trifluoroacetateHCID 58646841(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Product 1

HCID 12150904(4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.4 g of (5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate prepared in Example 1-f was dissolved in 30 ml of trifluoroacetic acid, and 5.0 g of thallium trifluoroacetate was added at room temperature in an atmosphere of nitrogen gas. The mixture was stirred at room temperature for 4 hours, followed by stirring at 50° C. for 2 hours. After the starting material disappeared, 3 ml of an aqueous solution of 1.5 g of potassium iodide was added to the reaction mixture and the mixture was stirred at room temperature for 0.5 hour. To the reaction mixture were added ethyl acetate and water, and the mixture was neutralized with sodium hydrogencarbonate and filtered through Celite. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:20), to give 4.1 g of a 3:1 mixture of the title compounds as a colorless oil.

Workup

  1. stirringby stirring at 50° C. for 2 hours
  2. stirringthe mixture was stirred at room temperature for 0.5 hour
  3. filtrationfiltered through Celite
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:20)
  9. customto give

Sources & evidence

ORD record
ord-beb1bafe3a1c4769af44e738bbebdf18
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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