N-bromobutanimide → 4-Bromo-7-methoxy-3-methyl-2-trifluoromethylbenzimidazole

HRID 275794

Reaktionsgleichung

Reaktionsgleichung von HRID 275794
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[N:11]([CH3:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:17][C:6]1[C:7]2[N:11]([CH3:12])[C:10]([C:13]([F:16])([F:14])[F:15])=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 183166367-Methoxy-3-methyl-2-trifluoromethylbenzimidazole

Produkt 1

HCID 183166224-Bromo-7-methoxy-3-methyl-2-trifluoromethylbenzimidazoleAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 7-methoxy-3-methyl-2-trifluoromethylbenzimidazole (1.4 g) in chloroform (50 ml) under nitrogen was added N-bromosuccinimide (1.2 g). The mixture was stirred for 20 minutes before the reaction was quenched by the addition of 5% sodium metabisulphite solution (50 ml) and the organic layer was separated. Washing with water (50 ml), drying over anhydrous magnesium sulphate and removal of the solvent in vacuo gave an orange oil. Purification by flash chromatography eluting with 50% ethyl acetate in hexane gave the title compound as an orange solid (1.73 g).

Aufarbeitung

  1. customwas quenched by the addition of 5% sodium metabisulphite solution (50 ml)
  2. customthe organic layer was separated
  3. washWashing with water (50 ml)
  4. dry with materialdrying over anhydrous magnesium sulphate and removal of the solvent in vacuo
  5. customgave an orange oil
  6. customPurification by flash chromatography
  7. washeluting with 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-de379988852f45a1b9e7d4a9df08a5f3
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353010B1

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