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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1295967Generated: October 30, 2026

Dimethylformamide → 1-[5-Bromo-3-(dimethylamino)-2-methoxyphenyl]-1-ethanone

https://huagongshe.com/reaction/1295967

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl iodideHCID 6328—
ReactantPotassium CarbonateHCID 11430—
Reactant1-(3-Amino-5-bromo-2-methoxy-phenyl)-ethanoneHCID 22929675—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product1-[5-Bromo-3-(dimethylamino)-2-methoxyphenyl]-1-ethanoneHCID 22929693—

Reaction Conditions

Temperature65 °C

Reaction Steps

A mixture of 1-(3-amino-5-bromo-2-methoxyphenyl)-1-ethanone (12.8 g), iodomethane (60 mL), potassium carbonate (14.4 g) and N,N-dimethylformamide (200 mL) was stirred at 60 to 70° C. for 2 hours. Water was added to the mixture, extraction was performed with ethyl acetate, and the organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (9.6 g) as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07244730B2
Source datasetuspto-grants-2007_07
ORD IDord-5f8f4b21fee84eb9a309debfaa76dac7
Source noteuspto-grants-2007_07