Water → 3,4-Dibromo-6-(trifluoromethyl)pyridazine

HRID 1400085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400085
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[N:4][C:3]=1O.P(Br)(Br)([Br:15])=O.O.C(=O)([O-])O.[Na+]>ClCCl>[Br:15][C:3]1[N:4]=[N:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=1[Br:1]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 178518920HCID 178518920, Verbindung

Produkt 1

HCID 592333853,4-Dibromo-6-(trifluoromethyl)pyridazineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 4-bromo-6-trifluoromethyl-pyridazin-3-ol (D3) (4.0 g, 16.4 mmol) and phosphorus oxybromide (28.2 g, 98.4 mmol) was stirred at 60° C. for 4 h. After this period, the reaction mixture was poured into a mixture of ice and water, diluted with dichloromethane and neutralized with a saturated solution of sodium hydrogen carbonate. The organic layer was separated, dried (MgSO4) and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. to yield D5 (2.28 g, 46%) as a solid. C5HBr2F3N2 requires 305; Found 306 (MH+).

Aufarbeitung

  1. waitAfter this period
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated in vacuo
  5. customThe crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane)
  6. customThe desired fractions were collected
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5e5d8b9d9bb84c4eae55723d312a8f7e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906921B2

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