Sodium Iodide → 3-bromo-4-(iodomethyl)-1-tert-pentyl-1H-pyrazole

HRID 711044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711044
[Br:1][C:2]1[C:6]([CH2:7]Cl)=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1.[I-:14].[Na+]>CC(C)=O>[Br:1][C:2]1[C:6]([CH2:7][I:14])=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 674915603-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole

Produkt 1

HCID 674914913-bromo-4-(iodomethyl)-1-tert-pentyl-1H-pyrazoleAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole (725 mg, 2.73 mmol) in acetone (25 mL) was added sodium iodide (4.09 g, 27.3 mmol). The reaction was heated at reflux for 2 hours, then cooled to room temperature and stirred overnight. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium thiosulfate and brine. The organics were dried over sodium sulfate, filtered, and concentrated to yield the title compound (824 mg, 85%) as a brown oil. 1H NMR (400 MHz, CDCl3, δ): 7.47 (s, 1H), 4.26 (s, 2H), 1.83 (q, J=7.41 Hz, 2H), 1.50 (s, 6H), 0.67 (t, J=7.51 Hz, 3H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated aqueous sodium thiosulfate and brine
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0ad89ed1e50a473892794ab08f92f321
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181252B2

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