Sodium Iodide → (5-Chloro-2-hydroxy-4-methoxy-phenyl)-(4-fluoro-phenyl)-methanone

HRID 493216Notes

Reaction equation

HRID 493216 reaction equation
[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([O:17]C)=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.[I-].[Na+].[Al+3].[Cl-].[Cl-].[Cl-]>C(#N)C>[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([OH:17])=[C:6]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6451240Aluminum(III) ChlorideHCID 68725924(5-Chloro-2,4-Dimethoxy-phenyl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 68725962(5-Chloro-2-hydroxy-4-methoxy-phenyl)-(4-fluoro-phenyl)-methanoneYield 86.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above prepared (5-chloro-2,4-Dimethoxy-phenyl)-(4-fluoro-phenyl)-methanone (8.41 g, 28.5 mmol) was dissolved in 115 mL of acetonitrile and treated successively with sodium iodide (6.51 g, 1.5 eq.) and AlCl3 (3.86 g, 1.0 eq.), and the mixture kept at 80° C. for 0.75 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by a short flash chromatography (SiO2, hexane/AcOEt=9/1), afforded 6.94 g of the title compound as light yellow solid.

Workup

  1. temperatureCooling
  2. additionpouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with brine
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-560d5d6328114f09afdce6043a43ba07
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

Loading…