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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 629295Generated: October 30, 2026

1,1'-Carbonyldiimidazole → 5-Bromo-6-(2,4-difluorophenoxy)-1,3-dihydro-2H-benzimidazol-2-one

https://huagongshe.com/reaction/629295

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
Reactant4-Bromo-5-(2,4-difluorophenoxy)benzene-1,2-diamineHCID 118093676—
SolventEthyl AcetateHCID 8857—
Product5-Bromo-6-(2,4-difluorophenoxy)-1,3-dihydro-2H-benzimidazol-2-oneHCID 11809367039%

Reaction Conditions

Temperature50 °C

Reaction Steps

A solution of 4-bromo-5-(2,4-difluorophenoxy)benzene-1,2-diamine (0.371 g, 1.18 mmol) in ethyl acetate (5.20 mL) was treated with N,N-carbonyldiimidazole (0.23 g, 1.4 mmol) and stirred at 50° C. for 30 min. The reaction mixture was treated with additional N,N-carbonyldiimidazole (1.2 eq) and stirred at 50° C. for 1 h. The reaction mixture was cooled to 20° C. and the heterogeneous mixture was filtered to give the desired product (156 mg, 39%) as a light grey solid. LCMS calculated for C13H8BrF2N2O2 (M+H)+: m/z=341.0, 343.0. found: 341.0, 342.9.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315501B2
Source datasetuspto-grants-2016_04
ORD IDord-c1d26d6cfcb74444942ccb70b51f5a20
Source noteuspto-grants-2016_04