(Diethylamino)sulfur trifluoride → 3-(4-Bromophenyl)-3-fluorooxetane

HRID 385722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385722
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:19])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([F:19])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 583823793-(4-Bromophenyl)oxetan-3-ol

Produkt 1

HCID 595256233-(4-Bromophenyl)-3-fluorooxetane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3-(4-Bromophenyl)oxetan-3-ol (1.55 g, 6.77 mmol) was taken up in DCM (100 mL) and cooled to −78° C. DAST (1.073 mL, 8.12 mmol) was added and the mixture was stirred at −78° C. for 90 minutes followed by 0° C. for 20 minutes. Saturated NaHCO3 was added and the products extracted into DCM (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes) gave the title compound as a yellow oil.

Aufarbeitung

  1. waitfollowed by 0° C. for 20 minutes
  2. extractionthe products extracted into DCM (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-868f88ee52db49e3b56337e79c238a3f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

Notizen zur Reaktion

Wird geladen…