Benzoyl Peroxide → 5-(Bromomethyl)-2-chloro-3-fluoropyridine

HRID 1851683

Reaktionsgleichung

Reaktionsgleichung von HRID 1851683
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=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:10][CH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 135413652-Chloro-3-fluoro-5-methylpyridine

Produkt 1

HCID 592970785-(Bromomethyl)-2-chloro-3-fluoropyridineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

2-chloro-3-fluoro-5-methylpyridine in an amount of 4.00 g (27.6 mmol) was dissolved in 80 mL of carbon tetrachloride, following which 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added and the mixture was refluxed overnight under heating. Following reaction completion, the reaction mixture was returned to room temperature, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane/ethyl acetate=19:1), giving 3.06 g of 5-(bromomethyl)-2-chloro-3-fluoropyridine (yield, 51%).

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was refluxed overnight
  3. temperatureunder heating
  4. customreaction completion
  5. customwas returned to room temperature
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography (hexane/ethyl acetate=19:1)

Quellen und Nachweise

ORD-Eintrag
ord-89c0e7f9ae704813bc970c6daeec7fbe
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957214B2

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