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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 352103Generated: October 28, 2026

Triphenylphosphine → 4-Chloro-2-[[(1r)-4-chloro-1-phenylbutyl]oxy]benzonitrile

https://huagongshe.com/reaction/352103

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Reactant4-Chloro-2-hydroxybenzonitrileHCID 3442789—
Reactant4-Chloro-2-[[(1R)-4-(methylamino)-1-phenylbutyl]oxy]benzonitrile ethanedioateHCID 86588346—
SolventTolueneHCID 1140—
SolventTetrahydrofuranHCID 8028—
Product4-Chloro-2-[[(1r)-4-chloro-1-phenylbutyl]oxy]benzonitrileHCID 69829345197.8%

Reaction Steps

Diethyl azodicarboxylate (1.86 g) was added dropwise to a solution of triphenylphosphine (2.81 g), 4-chloro-2-hydroxybenzonitrile (1.49 g) and the product from step (a) (1.79 g) in tetrahydrofuran (5 ml) and toluene (60 ml) at 0° C. and stirred at 0° C. for 4hand at 20° C. for 18 h. The solvent was removed in vacuo and the residue was purified by chromatography on silica eluting with hexane-diethyl ether (4:1) to give the title compound as a colourless oil (2.80 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06743939B2
Source datasetuspto-grants-2004_06
ORD IDord-ff1ee18df3204078b4bad0be70063c05
Source noteuspto-grants-2004_06