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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2098913Generated: October 30, 2026

Dimethylformamide → 4-(4-(Chloromethyl)-2-(5,5-dimethylcyclopent-1-enyl)phenyl)-5-fluoro-2-methoxypyridine

https://huagongshe.com/reaction/2098913

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantThionyl ChlorideHCID 24386—
Reactant(3-(5,5-Dimethylcyclopent-1-enyl)-4-(5-fluoro-2-methoxypyridin-4-yl)phenyl)methanolHCID 57467619—
SolventDichloromethaneHCID 6344—
Product4-(4-(Chloromethyl)-2-(5,5-dimethylcyclopent-1-enyl)phenyl)-5-fluoro-2-methoxypyridineHCID 57467620—

Reaction Steps

To (3-(5,5-dimethylcyclopent-1-enyl)-4-(5-fluoro-2-methoxypyridin-4-yl)phenyl)methanol T8.3 (34.5 mg, 105 μmol) was added DCM (1.1 mL) and DMF (8.2 μL, 105 μmol) followed by thionyl chloride (15 μL, 211 μmol) in an ice bath. The reaction was then stirred at room temperature for 1 hour. The reaction was concentrated and directly purified on silica gel to afford 4-(4-(chloromethyl)-2-(5,5-dimethylcyclopent-1-enyl)phenyl)-5-fluoro-2-methoxypyridine T8 (36 mg) as an oil (99%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08450522B2
Source datasetuspto-grants-2013_05
ORD IDord-7e766e8f11bb42fcae5724dc331d9540
Source noteuspto-grants-2013_05