Sodium Iodide → 4'-Fluoro-2-hydroxy-4-methoxybenzophenone

HRID 493206Notes

Reaction equation

HRID 493206 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:12].[I-].[Na+].[Al+3].[Cl-].[Cl-].[Cl-]>C(#N)C>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[OH:2])=[O:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6451240Aluminum(III) ChlorideHCID 19986218(2,4-Dimethoxyphenyl)(4-fluorophenyl)methanone

Product 1

HCID 771524'-Fluoro-2-hydroxy-4-methoxybenzophenoneYield 88.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above prepared (2,4-Dimethoxy-phenyl)-(4-fluoro-phenyl)-methanone (7.75 g, 29.8 mmol) was dissolved in 150 mL of acetonitrile and treated successively with sodium iodide (6.70 g, 1.5 eq.) and AlCl3 (3.97 g, 1.0 eq.), and the mixture kept at 80° C. for 1.5 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over sodium sulfate, and evaporation of the solvents, followed by a short flash chromatography (SiO2, hexane/AcOEt=9/1), gave 6.49 g of the title compound as yellow solid.

Workup

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

Sources & evidence

ORD record
ord-5ecd063f4b594347b3a365b051d70e4d
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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