Benzoyl Peroxide → 2-(Bromomethyl)-1-chloro-3-iodobenzene

HRID 1868932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868932
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[CH3:9].[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:3]1[C:4]([I:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27576171-Chloro-3-iodo-2-methylbenzene

Produkt 1

HCID 670999852-(Bromomethyl)-1-chloro-3-iodobenzeneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-chloro-3-iodo-2-methylbenzene (11 g, 44 mmol) in 60 mL CCl4 was stirred at 70° C. and treated with 1-bromopyrrolidine-2,5-dione (12 g, 65 mmol) and dibenzoyl peroxide (1.1 g, 4.4 mmol) slowly. The resulting mixture was refluxed for 15 hours. The mixture was cooled to room temperature, filtered through a plug of Celite, and washed with 10% EtOAc/hexane. The organic was concentrated and purified by column chromatography (0-10% EtOAc/hexane) to give 14 g pink solid.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 15 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through a plug of Celite
  4. washwashed with 10% EtOAc/hexane
  5. concentrationThe organic was concentrated
  6. custompurified by column chromatography (0-10% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-49cdd5f5e99a4f42bae99b7545f8827f
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635715B2

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