Hydrochloric Acid → 2,3-Dichloro-4-methoxy-4'-fluorobenzophenone

HRID 1439211

Reaction equation

HRID 1439211 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([C:6]2[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([Cl:1])[C:7]=2[Cl:8])=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 201506312,3-Dichloro-4-methoxy-4'-fluorobenzophenoneYield 53.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,3-dichloroanisole (35.4 g.; 0.20 mole), 4-fluorobenzoyl chloride (34.8 g.; 0.22 mole) and methylene chloride (300 ml.) at 5° C. was stirred vigorously and treated with finely powdered aluminum chloride (28.0 g.; 0.21 mole). The reaction mixture was slowly heated and refluxed for two hours. The reaction mixture was cooled to room temperature and decomposed with ice and hydrochloric acid (50 ml.). The aqueous solution was extracted twice with methylene chloride. The combined methylene chloride solution was washed with aqueous sodium bicarbonate solution and finally with water. The organic layer was dried (MgSO4) and filtered. The solvent was removed in vacuo, and the residue on triturating with pet. ether gave the product 32 g. (50%); m.p. 138°-140°. This product was used for Step B without further purification.

Workup

  1. temperatureThe reaction mixture was slowly heated
  2. temperaturerefluxed for two hours
  3. extractionThe aqueous solution was extracted twice with methylene chloride
  4. washThe combined methylene chloride solution was washed with aqueous sodium bicarbonate solution and finally with water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue on triturating with pet. ether

Sources & evidence

ORD record
ord-e544f0f0bcf4412dbc23835a0109dfb9
Source dataset
uspto-grants-1977_11
Patent number
US04058559

Linked notes

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