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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1662393Generated: October 29, 2026

Thionyl Chloride → 4'-(Chloromethyl)-6-fluoro-2'-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-3-yl methyl ether

https://huagongshe.com/reaction/1662393

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant(2'-Fluoro-5'-(methyloxy)-2-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-4-yl)methanolHCID 57706974—
SolventDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
Product4'-(Chloromethyl)-6-fluoro-2'-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-3-yl methyl etherHCID 5770716595%

Reaction Steps

To a stirred solution of 66.15F (0.035 g, 0.10 mmol) in DCM (2.00 mL) and DMF (0.01 mL) at 0° C. was added thionyl chloride (0.01 g, 0.10 mmol). The reaction was then stirred at room temperature for 2 hours and was then concentrated in vacuo. The resulting product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.15G as a colorless oil (0.035 g, 95% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08030354B2
Source datasetuspto-grants-2011_10
ORD IDord-368d4acef3564f029c6cad1df277215f
Source noteuspto-grants-2011_10