Benzoyl Peroxide → 5-(Bromomethyl)-2-(trifluoromethyl)pyridine

HRID 622710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622710
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:10][C:8]([F:11])([F:9])[C:5]1[CH:4]=[CH:3][C:2]([CH2:1][Br:12])=[CH:7][N:6]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 144227915-Methyl-2-(trifluoromethyl)pyridine

Produkt 1

HCID 144051255-(Bromomethyl)-2-(trifluoromethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

5-Methyl-2-trifluoromethylpyridine (see J. Org. Chem., vol. 29, pages 569-571) (8.1 g) was dissolved in 50 ml of carbon tetrachloride, and N-bromosuccinimide (8.9 g) and a catalytic amount of benzoyl peroxide were added. The mixture was refluxed for 7 hours with stirring. The reaction mixture was cooled, and insoluble materials were collected by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 2-trifluoromethyl-5-pyridylmethyl bromide (also known as 5-bromomethyl-2-trifluoromethylpyridine) (7.3 g).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 7 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationinsoluble materials were collected by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-40f2620b54a34a33819f77c0004ce333
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04772620

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