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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1051453Generated: November 1, 2026

p-Toluenesulfonic acid monohydrate → 6-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazole

https://huagongshe.com/reaction/1051453

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acid monohydrateHCID 521998—
Reactant5-bromo-N-(4-methoxybenzyl)benzene-1,2-diamineHCID 65343343—
SolventTrimethyl orthoformateHCID 9005—
Product6-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazoleHCID 86729242886.7%

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of 5-bromo-N-(4-methoxybenzyl)benzene-1,2-diamine (550 mg, crude) in HC(OMe)3 (20 mL) was added TsOH.H2O (30 mg, 0.16 mmol). The mixture was stirred at 100° C. for 4 h. The reaction solution was then concentrated and the residue was washed with water and extracted with EtOAc. The organic layer was concentrated to give the desired product (450 mg, 79% yield) and the crude product used in next step without further purification. LCMS (m/z): 318.1 [M+H]+

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09388173B2
Source datasetuspto-grants-2016_07
ORD IDord-a05593659c7f4edbae89920f621473e6
Source noteuspto-grants-2016_07