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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 969528Generated: November 2, 2026

Water → 4-Benzyloxy-6-bromo-1-methoxymethyl-2-methyl-1H-benzimidazole

https://huagongshe.com/reaction/969528

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantChloromethyl Methyl EtherHCID 7864—
ReactantSodium hydrideHCID 24758—
Reactant7-(benzyloxy)-5-bromo-2-methyl-1H-benzo[d]imidazoleHCID 67220214—
SolventDimethylformamideHCID 6228—
Product4-Benzyloxy-6-bromo-1-methoxymethyl-2-methyl-1H-benzimidazoleHCID 6913523826.4%

Reaction Conditions

Temperature0 °C

Reaction Steps

2.0 g (6.3 mmol) 4-Benzyloxy-6-bromo-2-methyl-1H-benzimidazole were solved in dimethylformamide (10 ml) and the solution was cooled to 0° C. 151 mg (6.5 mmol) sodium hydride (60%) were added in portions and the reaction was stirred for 20 min. 435 μl (6.3 mmol) 1-Chloro-1-methoxy-methane were added and the reaction was stirred at 0° C. After 2 h the mixture was poured into water (200 ml) and extracted with ethyl acetate. The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=6:1) to afford 0.6 g (26%) of the title compound as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07307084B2
Source datasetuspto-grants-2007_12
ORD IDord-0e4e6c3d99c64eb5bf8d5d65fa1fc9d2
Source noteuspto-grants-2007_12