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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1051451Generated: November 3, 2026

4-Methoxybenzylamine → 5-bromo-N-(4-methoxybenzyl)-2-nitroaniline

https://huagongshe.com/reaction/1051451

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-MethoxybenzylamineHCID 75452—
Reactant4-Bromo-2-fluoro-1-nitrobenzeneHCID 2783362—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product5-bromo-N-(4-methoxybenzyl)-2-nitroanilineHCID 6534167398%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (500 mg, 2.27 mmol) in DMF (6 mL) was added (4-methoxyphenyl)methanamine (342 mg, 2.5 mmol) and TEA (345 mg, 3.4 mmol). The reaction mixture was then stirred at 120° C. for 30 min under microwave heating. After cooling, the mixture was diluted with water (40 mL) and the resulting precipitate collected by filtration, washed with water and dried in vacuo to give the desired product (750 mg, crude, 97% yield) which was used in next step without further purification. LCMS (m/z): 338.1 [M+H]+

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09388173B2
Source datasetuspto-grants-2016_07
ORD IDord-9fcfd0cf818146d08227ce4cf5012721
Source noteuspto-grants-2016_07