2-Fluorobenzoyl chloride → 2,3-Dichloro-4-(2-fluorobenzoyl)phenetole

HRID 1154593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1154593
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH3:11].[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[F:12])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH3:11]

Komponenten

5

Edukt 3

HCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 104200611,2-Dichloro-3-ethoxybenzene

Produkt 1

HCID 133437072,3-Dichloro-4-(2-fluorobenzoyl)phenetoleAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2,3-dichlorophenetole (57.3 g., 0.3 mole), 2-fluorobenzoyl chloride (47.8 g., 0.3 mole) and methylene chloride (300 ml.) at 5° C. was stirred vigorously and treated with finely powdered aluminum chloride (42.6 g., 0.32 ml.). The reaction mixture was slowly warmed to room temperature and then stirred overnight. The reaction mixture was decomposed with ice/concentrated hydrochloric acid (50 ml.) and the aqueous solution was extracted twice with methylene chloride. The combined organic extracts were washed with aqueous sodium bicarbonate solution and finally with aqueous sodium chloride solution. The methylene chloride solution was dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue on triturating with methanol gave the product 55 g., m.p. 94°-95° C. This material was used in the next step without additional purification.

Aufarbeitung

  1. stirringstirred overnight
  2. extractionthe aqueous solution was extracted twice with methylene chloride
  3. washThe combined organic extracts were washed with aqueous sodium bicarbonate solution and finally with aqueous sodium chloride solution
  4. dry with materialThe methylene chloride solution was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe residue on triturating with methanol

Quellen und Nachweise

ORD-Eintrag
ord-6957526e7ec64774994257037395d6e5
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04490384

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