Cyclohexanecarbonyl chloride → Cyclohexyl 2-Fluorobenzyl Ketone

HRID 1789991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789991
[Cl-].[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Zn+].[CH:11]1([C:17](Cl)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][C:17]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:18]

Komponenten

4

Edukt 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 178505630HCID 178505630, Verbindung

Produkt 1

HCID 22037180Cyclohexyl 2-Fluorobenzyl Ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418476HCID 178418476, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 36 ml of 2-fluorobenzylzinc chloride (0.5 M sol. in tetrahydrofuran) and 0.008 g of dichlorobis(triphenylphosphine)palladium(II) stirred at 0° C. was added dropwise via a syringe 2.14 ml of cyclohexanecarbonyl chloride. Afterwards, the reaction mixture was stirred at r.t. for 4 h, quenched with an aqueous saturated solution of ammonium chloride (25 ml), extracted with 20 ml of EtOAc, which was dried (Na2SO4) and evaporated to dryness in vacuo affording 3.52 g of the title compound as a crude, which could be used in the following step without further purification.

Aufarbeitung

  1. stirringAfterwards, the reaction mixture was stirred at r.t. for 4 h
  2. customquenched with an aqueous saturated solution of ammonium chloride (25 ml)
  3. extractionextracted with 20 ml of EtOAc, which
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee37b3bbe8884342a72654bff4d2cc0e
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071197B2

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