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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1661884Generated: October 28, 2026

Water → 4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

https://huagongshe.com/reaction/1661884

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactant2-Bromoethyl methyl etherHCID 80972—
Reactant4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazoleHCID 57772015—
SolventDimethylformamideHCID 6228—
Product4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazoleHCID 11281119563.9%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a stirred solution of 500 mg (1.45 mmol) 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole in 11 ml DMF, NaH (38 mg, 1.6 mmol) is added and stirring is continued for 1 h at RT, and then the reaction mixture is heated to 60° C. 0.152 ml (0.175 mmol) (2-bromoethyl)-methyl ether is added and stirring is continued at this temperature for another 6 h. The reaction mixture is cooled to room temperature, poured into water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 398 mg of the title compound as colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08030497B2
Source datasetuspto-grants-2011_10
ORD IDord-faba9025e5e64145b6850c1c74659af8
Source noteuspto-grants-2011_10