4-Fluorobenzoyl chloride → (5-Chloro-2,4-Dimethoxy-phenyl)-(4-fluoro-phenyl)-methanone

HRID 493215Notes

Reaction equation

HRID 493215 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].[Al+3].[Cl-].[Cl-].[Cl-].[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[CH:4][C:5]([O:8][CH3:9])=[C:6]([C:21]([C:20]2[CH:24]=[CH:25][C:17]([F:16])=[CH:18][CH:19]=2)=[O:22])[CH:7]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 1389051-Chloro-2,4-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68725924(5-Chloro-2,4-Dimethoxy-phenyl)-(4-fluoro-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Chloro-2,4-Dimethoxy-benzene (5.00 g, 29.0 mmol) and AlCl3 (4.63 g, 1.2 eq.) were dissolved in 290 ml of CH2Cl2 and cooled down to 0° C. 4-Fluoro-benzoyl chloride (3.47 mL, 1.0 eq.) was slowly added via dropping funnel and the mixture allowed to react for 2 additional h at ambient temperature. Pouring onto crashed ice, twofold extraction with AcOEt, washing with brine, drying over sodium sulfate, and evaporation of the solvents left 8.41 g of the title compound used crude for the next step.

Workup

  1. customto react for 2 additional h at ambient temperature
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with brine
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. waitleft 8.41 g of the title compound used crude for the next step

Sources & evidence

ORD record
ord-accd5c821e0143a581c609c9ff49b0f1
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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