Benzoyl Peroxide → Ethyl 3-(bromomethyl)-2-chloroisonicotinate

HRID 715207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 715207
[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:3]1[C:2]([Cl:1])=[N:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2762478Ethyl 2-chloro-3-methylisonicotinate

Produkt 1

HCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinateAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-chloro-3-methylisonicotinate (4.0 g, 20.0 mmol), N-bromosuccinimide (3.7 g, 21.0 mmol), and dibenzoyl peroxide (0.49 g, 2.0 mmol) in carbon tetrachloride (50 mL) is heated at reflux temperature for 2 hours. After cooling to rt, the reaction mixture (suspension) is filtered through a pad of Celite™ (Celite Corporation), and washed with carbon tetrachloride. The filtrate is concentrated to give clear yellow oil. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (10:1) to give 4.1 g (73% yield) of the title compound as a clear yellow liquid.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. filtrationthe reaction mixture (suspension) is filtered through a pad of Celite™ (Celite Corporation)
  4. washwashed with carbon tetrachloride
  5. concentrationThe filtrate is concentrated
  6. customto give clear yellow oil
  7. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-a9655879d9bd47989abac2e9e1b3d2b0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187475B2

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