Pyridine → 6-Bromonaphthalene-2-carbonitrile

HRID 2407447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407447
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH2:14])=O)[CH:6]=[CH:5]2.N1C=CC=CC=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[N:14])[CH:6]=[CH:5]2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 574280376-Bromo-2-naphthamide

Produkt 1

HCID 146621156-Bromonaphthalene-2-carbonitrileAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To 6-bromo-2-naphthamide (1 g, 4.00 mmol) in dioxane (8.00 ml) at 0° C. was added pyridine (0.647 ml, 8.00 mmol) and then TFAA (0.621 ml, 4.40 mmol) dropwise. The reaction was stirred at room temperature for 3 h. The mixture was quenched with H2O and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The title compound (653 mg, 70%) was isolated as a beige solid, and used as is for the next step.

Aufarbeitung

  1. customThe mixture was quenched with H2O
  2. extractionextracted with EtOAc two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2e895bf60af240438f8a199a99a86146
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809545B2

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