4-Chlorobutyryl chloride → 4-Chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone

HRID 51020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51020
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH3:9])[CH:3]=1.[Cl:10][CH2:11][CH2:12][CH2:13][C:14](Cl)=[O:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Cl:10][CH2:11][CH2:12][CH2:13][C:14]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[S:8][CH3:9])=[O:15]

Komponenten

5

Edukt 3

HCID 783704-Chlorobutyryl chlorideHCID 27591643-FluorothioanisoleHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 227354674-Chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanoneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 1-fluoro-3-(methylsulfanyl)benzene (1.98 g, 14.0 mmol) and 4-chlorobutyryl chloride in CH2Cl2 (15 mL) was added AlCl3 (2.06 g, 15.4 mmol) at 20° C. under N2. The reaction mixture was stirred for 15 h at 20° C. for 12 h then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystalized to give 4-chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone (2.80 g, 81%) as a white needle shape crystal.

Aufarbeitung

  1. customthen quenched by addition of H2O
  2. extractionextracted with Et2O
  3. washThe combine organic solution was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting white solid was recrystalized

Quellen und Nachweise

ORD-Eintrag
ord-52117471ca8744eba1dbbdcd014fc543
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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