Hydrochloric Acid → 1-(2-Fluoro-4,6-dimethoxyphenyl)propane-1-one

HRID 601654Notes

Reaction equation

HRID 601654 reaction equation
ClC(Cl)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([F:15])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.[C:16](Cl)(=[O:19])[CH2:17][CH3:18].Cl>[Cl-].[Cl-].[Zn+2]>[F:15][C:9]1[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[C:16](=[O:19])[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63651,1-Dichloroethane3×HCID 62324Propionyl chlorideHCID 27742571-Fluoro-3,5-dimethoxybenzene

Product 1

HCID 231582391-(2-Fluoro-4,6-dimethoxyphenyl)propane-1-oneYield 50,306.301%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Under nitrogen atmosphere, 5 ml solution of dichloroethane with 2 g of 3,5-dimethoxy-1-fluorobenzene, and 5 ml solution of dichloroethane with 1.3 mg of propionyl chloride were dropped sequentiallly at −10° C. to 40 ml solution of dichloroethane with 2.4 g of alumimium trichloride and 240 mg of zinc dichloride, and the mixture was stirred at room temperature for 2 hours. 20% hydrochloric acid aqueous solution was added to the reaction solution, extracted with chloroform. Chloroform layer was washed with saturated saline solution, dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure and the residues were separated and purified by silicagel chromatography (hexane/ethyl acetate=5/1), to obtain 1.5 g of the above compound as a white solid.

Workup

  1. extractionextracted with chloroform
  2. washChloroform layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvents were distilled outunder reduced pressure
  5. customthe residues were separated
  6. custompurified by silicagel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-d5fe795567fc4587aca9f1869ce9b2bc
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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