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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2414420Generated: November 2, 2026

Ethyl Acetate → 4-iodo-3-[(2R)-(1-t-butoxycarbonyl-pyrrolidine-2-ylmethoxy)]benzonitrile

https://huagongshe.com/reaction/2414420

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantPotassium CarbonateHCID 11430—
Reactant3-Hydroxy-4-iodobenzonitrileHCID 10944681—
Reactant1-t-butoxycarbonyl-(2R)-2-(p-tolylmethanesulfonyloxymethyl)pyrrolidineHCID 86584113—
SolventDimethylformamideHCID 6228—
Product4-iodo-3-[(2R)-(1-t-butoxycarbonyl-pyrrolidine-2-ylmethoxy)]benzonitrileHCID 69924444—

Reaction Conditions

Temperature50 °C

Reaction Steps

2.0 g (8.16 mmol) of 3-hydroxy-4-iodobenzonitrile was dissolved in 20 ml of DMF. 5.8 g (16.3 mmol) of 1-t-butoxycarbonyl-(2R)-2-(p-tolylmethanesulfonyloxymethyl)pyrrolidine and 3.37 g (24.4 mmol) of potassium carbonate were added to the obtained solution, and they were stirred at 50° C. for 16 hours. 1.5 g (4.2 mmol) of 1-t-butoxycarbonyl-(2R)-2-(p-tolylmethanesulfonyloxymethyl)pyrrolidine was added to the obtained mixture, and they were stirred at 50° C. for 4 hours. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06812231B2
Source datasetuspto-grants-2004_11
ORD IDord-e4d699ca004148779eafa0c3d74142be
Source noteuspto-grants-2004_11