Potassium Iodide → HCID 86604223, compound

HRID 1452694Notes

Reaction equation

HRID 1452694 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:27].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[CH2:28]([O:27][C:3]1[CH:4]=[CH:5][C:6]([C:8]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=1[Cl:1])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86604224HCID 86604224, compound

Product 1

HCID 86604223HCID 86604223, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

100 mg (0.2 mmol) of 2-chloro-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol (example 3) in 4 ml of acetone were treated with 47 mg (0.3 mmol) of benzyl bromide, 157 mg (0.5 mmol) of Cs2CO3 and 4 mg (0.025 mmol) of potassium iodide. The reaction mixture was stirred at 50° C. overnight, cooled to room temperature, filtered and the solvent was evaporated. The residue was dissolved in EtOAc and water, the phases were separated and the inorganic one was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to give 82 mg (67%) of crude 1-benzyloxy-2-chloro-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-benzene.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in EtOAc
  5. customwater, the phases were separated
  6. extractionthe inorganic one was extracted with EtOAc
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-6f177dabe4444577a6437ee392f8a956
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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