N-bromobutanimide → 3-Bromo-5-(bromomethyl)-2-fluoropyridine

HRID 1811850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811850
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[C:11]([F:17])=[N:12][CH:13]=[C:14]([CH3:16])[CH:15]=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][C:10]1[C:11]([F:17])=[N:12][CH:13]=[C:14]([CH2:16][Br:1])[CH:15]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 218165633-Bromo-2-fluoro-5-methylpyridine

Produkt 1

HCID 595482443-Bromo-5-(bromomethyl)-2-fluoropyridineAusbeute 22,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (4.732 g, 26.59 mmol) and benzoyl peroxide (0.1356 g, 0.5598 mmol) were added to a solution of 3-bromo-2-fluoro-5-methylpyridine (Matrix Innovation Inc., Montreal, Quebec, Canada 5.318 g, 27.99 mmol) in CCl4 (50 mL), and the mixture was heated at gentle reflux under a N2 atmosphere for 16 h. The mixture was filtered, washing with CCl4, and the residue concentrated and purified by flash chromatography on silica (1% to 1.5% EtOAc/hexane) to give 3-bromo-5-(bromomethyl)-2-fluoropyridine (1.593 g, 21.17% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H); 8.03 (dd, J=8.02, 2.15 Hz, 1H); 4.43 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −65.17 (br. s., 1 F). Sample did not ionize well in ESI+ mode.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat gentle reflux under a N2 atmosphere for 16 h
  3. filtrationThe mixture was filtered
  4. washwashing with CCl4
  5. concentrationthe residue concentrated
  6. custompurified by flash chromatography on silica (1% to 1.5% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-037c99602c8a45589a62da7d060141a1
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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