Benzoyl Peroxide → 3-Bromo-5-(bromomethyl)-2-chloropyridine

HRID 633592

Reaktionsgleichung

Reaktionsgleichung von HRID 633592
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([CH2:8][Br:10])[CH:7]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2854373-Bromo-2-chloro-5-methylpyridine

Produkt 1

HCID 848198723-Bromo-5-(bromomethyl)-2-chloropyridineAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3-Bromo-2-chloro-5-methylpyridine (4 g, 19.37 mmol), N-bromosuccinimide (3.79 g, 21.3 mmol) and benzoic peroxyanhydride (0.239 g, 0.969 mmol) were combined in carbon tetrachloride (40 mL), heated under reflux for 24 hours, cooled, and filtered to remove succinimide. The filtrate was concentrated. The resulting residue was purified by chromatography (silica gel, 0-30% ethyl acetate in heptanes) to afford the title compound (1.9 g, 34%).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove succinimide
  6. concentrationThe filtrate was concentrated
  7. customThe resulting residue was purified by chromatography (silica gel, 0-30% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-5f1e9721a6ad4763840e47cbb6a5ba51
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321764B2

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