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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 474677Generated: October 30, 2026

Tetrahydrofuran → 1-Chloro-3-[(4-ethenylphenyl)oxy]-5-(trifluoromethyl)benzene

https://huagongshe.com/reaction/474677

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantSodium hydrideHCID 24758—
Reactant4-{[3-Chloro-5-(trifluoromethyl)phenyl]oxy}benzaldehydeHCID 86666212—
CatalystMethyltriphenyliphosphonium bromideHCID 74505—
Product1-Chloro-3-[(4-ethenylphenyl)oxy]-5-(trifluoromethyl)benzeneHCID 6777693980%

Reaction Steps

To a stirred suspension of 4-{[3-chloro-5-(trifluoromethyl)phenyl]oxy}benzaldehyde (3.3 g, 10.98 mmol) and methyl(triphenyl)phosphonium bromide (3.92 g, 10.98 mmol) in dry THF (30 mL) was added NaH (1.536 g, 38.4 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 2 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (2.63 g, 8.81 mmol, 80% yield) as a light green oil. LCMS: rt=4.45 min, [M+H+]=324

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08637536B2
Source datasetuspto-grants-2014_01
ORD IDord-5a92caf66ccf447fac185f37a48ddeca
Source noteuspto-grants-2014_01