(Diethylamino)sulfur trifluoride → 2-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine

HRID 386066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386066
[Br:1][C:2]1[N:7]=[C:6]([CH:8](O)[C:9]#[CH:10])[CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:18])CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]([F:18])[C:9]#[CH:10])[N:7]=1

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 595262091-(6-Bromopyridin-2-yl)prop-2-yn-1-ol

Produkt 1

HCID 595259492-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(6-Bromopyridin-2-yl)prop-2-yn-1-ol (1.06 g, 5.00 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. Diethylaminosulfur trifluoride (925 μL, 7.00 mmol) was added dropwise, and the brown solution was stirred at 0° C. for 1 h. The reaction was quenched with saturated NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (0-15% EtOAc/hexanes) afforded the title compound as an orange oil.

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d727831c422c4015b5e82bee9319799d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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