Benzimidazole → 2-Benzoimidazol-1-yl-1-(3-bromophenyl)ethanone

HRID 659701Notes

Reaction equation

HRID 659701 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)=[O:4].[N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH:13]=1>O1CCOCC1>[N:12]1([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=2)=[O:4])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 5798BenzimidazoleHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Product 1

HCID 432182762-Benzoimidazol-1-yl-1-(3-bromophenyl)ethanoneYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-1-(3-bromophenyl)ethanone (120 mg, 0.432 mmol) in dioxane (2 mL) was added benzoimidazole (102.0 mg, 0.864 mmol) and the reaction mixture was stirred for 1 h at 80° C. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography using MeOH:CH2Cl2 (4:96) as eluent to give the sub-title compound in 53% yield (71.8 mg, 0.227 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-24c4467ba64745feaecdd792f027195b
Source dataset
uspto-grants-2011_12
Patent number
US08080571B2

Reaction notes

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