Potassium Cyanide → 5-(4-Fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthalene

HRID 1858008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1858008
[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[C:17](OS(C(F)(F)F)(=O)=O)=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1.[C-:32]#[N:33].[K+]>O1CCOCC1.[Cl-].[Na+].O.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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:17]([C:32]#[N:33])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:30][CH:31]=1

Komponenten

6

Edukt 2

HCID 9032Potassium CyanideHCID 221256945-(4-Fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene

Produkt 1

HCID 99284855-(4-Fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthaleneAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 5-(4-fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene (2.5 g, 5.2 mmol) [prepared as described in step 1 above], potassium cyanide (0.41 g, 6.3 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.30 g, 0.26 mmol) in dioxane (50 ml) was heated at reflux under argon. After 16 h, the reaction mixture was cooled to RT, poured into brine, and the product wias extracted into ethyl acetate. The organic layer was dried with sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution, 10-60% ethyl acetate/hexane) and then recrystallized from ethyl acetate-hexane to give 1.16 g of 5-(4-fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthalene as a solid (63% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under argon
  3. extractionthe product wias extracted into ethyl acetate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (gradient elution, 10-60% ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3ced89916d9e48139bb5831275ff9a2d
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150397

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