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

HRID 2235389

Reaktionsgleichung

Reaktionsgleichung von HRID 2235389
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27628635-Fluoro-2-methylpyridine

Produkt 1

HCID 247293132-(Bromomethyl)-5-fluoropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 5-fluoro-2-methyl-pyridine (0.75 g) (J. Med. Chem. 1989, 32, 1970) in CCl4 (25 ml) is added N-bromosuccinimide (0.96 g; 5.4 mmol) and benzoyl peroxide (200 mg; 0.8 mmol). The mixture is heated at reflux for 3 h, cooled to RT and stirred for additional 12 h. The suspension is filtered through celite and the filtrate is washed with Na2SO4, dried over MgSO4 and evaporated. The crude material (0.22 g) containing approximately 50% of the dibrominated species is used without further purification.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 h
  3. filtrationThe suspension is filtered through celite
  4. washthe filtrate is washed with Na2SO4
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additionThe crude material (0.22 g) containing approximately 50% of the dibrominated species
  8. customis used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-38844669a7d5413e81148bcc4f606c06
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714010B2

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