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

HRID 275794Notes

Reaction equation

HRID 275794 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-de379988852f45a1b9e7d4a9df08a5f3
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Reaction notes

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