Sodium Azide → 4-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine

HRID 407217

Reaktionsgleichung

Reaktionsgleichung von HRID 407217
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH:11]([F:13])[F:12].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C>[N:14]([C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH:11]([F:13])[F:12])=[N+:15]=[N-:16]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 86675402HCID 86675402, Verbindung

Produkt 1

HCID 866754034-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridineAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

4,6-Dibromo-2-chloro-3-(difluoromethoxy)pyridine (780 mg, 2.312 mmol) was dissolved in DMF (5 mL), and sodium azide (180 mg, 2.77 mmol) was added. The reaction mixture was heated at 65° C. for 2 h and the progress of the reaction was checked by liquid chromatography-mass spectrometry (LC-MS). The reaction appeared to be mostly complete. The product was partitioned between Et2O and H2O. The aqueous phase was then extracted twice more with Et2O. The organic extracts were combined, diluted with petroleum ether, washed twice with H2O, dried, and concentrated. The product was purified by column chromatography (SiO2, EtOAc/hexane gradient) to yield 4-azido-6-bromo-2-chloro-3-(difluoromethoxy)-pyridine (0.335 g, 48.4%): 1H NMR (300 MHz, CDCl3) δ 7.26 (s, 1H), 6.59 (t, J=73.6, 1H).

Aufarbeitung

  1. customThe product was partitioned between Et2O and H2O
  2. extractionThe aqueous phase was then extracted twice more with Et2O
  3. additiondiluted with petroleum ether
  4. washwashed twice with H2O
  5. customdried
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography (SiO2, EtOAc/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-936a03b1ed174943acf86b9cf6c1e710
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754229B2

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