1,3-Dimethoxybenzene → (2,4-Dimethoxyphenyl)(4-fluorophenyl)methanone

HRID 493205Notes

Reaction equation

HRID 493205 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][C:8]=1[C:20]([C:19]1[CH:23]=[CH:24][C:16]([F:15])=[CH:17][CH:18]=1)=[O:21]

Participants

5

Reactant 3

HCID 90251,3-DimethoxybenzeneHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19986218(2,4-Dimethoxyphenyl)(4-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,3-Dimethoxybenzene (5.00 g, 36.2 mmol) and AlCl3 (5.79 g, 1.2 eq.) were dissolved in 360 ml of CH2Cl2 and cooled down to 0° C. 4-Fluoro-benzoyl chloride (4.34 mL, 1.0 eq.) was slowly added via dropping funnel and the mixture allowed to react for another h at ambient temperature. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over sodium sulfate, and evaporation of the solvents, followed by short flash chromatography (SiO2, hexane/AcOEt 8/2), yielded 7.75 g of the title compound as white solid.

Workup

  1. customto react for another h at ambient temperature
  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-589f390c11b342adb74d5a7a84711aa6
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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