Azobisisobutyronitrile → 2-Chloro-5-(chloromethyl)-3-fluoropyridine

HRID 659972

Reaktionsgleichung

Reaktionsgleichung von HRID 659972
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[Cl:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][Cl:10])=[CH:4][C:3]=1[F:9]

Komponenten

5

Edukt 3

HCID 6547Azobisisobutyronitrile2×HCID 31398Chlorosuccinimide2×HCID 135413652-Chloro-3-fluoro-5-methylpyridine

Produkt 1

HCID 216982012-Chloro-5-(chloromethyl)-3-fluoropyridineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

1.00 g (6.87 mmol) of 6-chloro-5-fluoro-3-methylpyridine (cf. F. L. Setliff, Organic Preparations and Procedures International 1971, 3, 217-222), 1.01 g (7.56 mmol) of N-chlorosuccinimide and 0.11 g (0.69 mmol) of 2,2′-azobis(2-methylpropanenitrile) in 100 ml of chlorobenzene are boiled under reflux for 2 days. After about 16 and 32 hours, in each case a further 1.01 g (7.56 mmol) of N-chlorosuccinimide and 0.11 g (0.69 mmol) of 2,2′-azobis(2-methylpropanenitrile) are added. The reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution and then dried over sodium sulphate and concentrated under reduced pressure. Column chromatography of the residue on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:20) gives 0.65 g (53% of theory) 6-chloro-3-chloromethyl-5-fluoropyridine.

Aufarbeitung

  1. temperatureunder reflux for 2 days
  2. washThe reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7543eb0e29654cb8b29638f4505a423d
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084452B2

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