2,4-Dichlorobenzoyl chloride → 2',4'-Dichlorobutyrophenone

HRID 31753

Reaktionsgleichung

Reaktionsgleichung von HRID 31753
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([Mg]Cl)[CH2:13][CH3:14]>C1COCC1.[Cu]I>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](=[O:5])[CH2:12][CH2:13][CH3:14]

Komponenten

5

Edukt 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 178455855HCID 178455855, Verbindung

Produkt 1

HCID 131756172',4'-Dichlorobutyrophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A mixture of 2,4-dichlorobenzoyl chloride (4.5 g) and copper (I) iodide (200 mg) in dry THF (30 ml) was cooled to −20° C. under argon. Then a solution of n-propyl magnesium chloride (2 M in ether, 11.0 ml) was added dropwise. Ten minutes after addition was complete, the cooling bath was removed and the mixture stirred for 1 hour. Water was carefully added, followed by extraction with toluene. The toluene layer was washed with dilute HCl, water, saturated sodium bicarbonate solution, dried and concentrated in vacuo to give 1-(2,4-dichlorophenyl)butan-1-one (4.0 g).

Aufarbeitung

  1. additionTen minutes after addition
  2. customthe cooling bath was removed
  3. additionWater was carefully added
  4. extractionfollowed by extraction with toluene
  5. washThe toluene layer was washed with dilute HCl, water, saturated sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-06cb637d24334ae382e85a7f4772c423
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425557B2

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