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Cerium(III) chloride → 5-Bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone

HRID 1514607
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514607
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=2[Cl:17])=[O:9])=[CH:4][CH:3]=1.[CH2:18]([Al](CC)CC)[CH3:19].[Cl-].[Ce+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>O1CCCC1.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:18]([C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=2[Cl:17])=[O:9])=[CH:4][CH:3]=1)[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 24636Cerium(III) chlorideHCID 516892Sodium BicarbonateHCID 16682930TriethylaluminumHCID 469303355-Bromo-2-chlorophenyl 6-bromo-3-pyridyl ketone

Produkt 1

HCID 469305245-Bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 887MethanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

5-Bromo-2-chlorophenyl 6-bromo-3-pyridyl ketone (3.2 g) from Reference Example 135-(2) was dissolved in tetrahydrofuran (80 ml), and added thereto were triethylaluminium (1.0 M hexane solution, 9.9 ml), tetrakis(triphenylphosphine)palladium(0) (570 mg) and cerium(III) chloride (7.3 g), and the mixture was stirred at 30° C. for 1.5 hours. The reaction mixture was diluted with methanol, and the reaction solution was basified with a saturated aqueous sodium hydrogen carbonate solution. The insoluble materials were filtered off and, the filtrate was extracted with ethyl acetate and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-85:15) to give 5-bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone (1.98 g) as a colorless solid. APCI-Mass m/Z 324/326 (M+H). (2) The above 5-bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone was treated in a manner similar to Reference Example 14-(1) to give the desired 5-bromo-2-chloro-1-(6-ethyl-3-pyridylmethyl)benzene as a colorless oil. APCI-Mass m/Z 310/312 (M+H).

Aufarbeitung

  1. additionadded
  2. filtrationThe insoluble materials were filtered off
  3. extractionthe filtrate was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-85:15)

Quellen und Nachweise

ORD-Eintrag
ord-7e115e6e564847a6abd930af60eb2756
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222219B2

Notizen zur Reaktion

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