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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 561452Erstellt: 25. Oktober 2026

Diethyl Ether → 2-(4-Chloro-2-methoxybenzoyl)cyclopropanecarbonitrile

https://huagongshe.com/reaction/561452

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDiethyl EtherHCID 3283—
Edukt2-Bromo-4-chloroanisoleHCID 521935—
EduktMagnesiumHCID 5462224—
Edukt2-Cyano-N-methoxy-N-methylcyclopropanecarboxamideHCID 58392506—
Katalysator1,1-DibromoethaneHCID 11201—
LösungsmittelTetrahydrofuranHCID 8028—
LösungsmittelEthyl AcetateHCID 8857—
Produkt2-(4-Chloro-2-methoxybenzoyl)cyclopropanecarbonitrileHCID 58392548—

Reaktionsschritte

A solution of 500 mg (2.26 mmol) of 2-bromo-4-chloroanisole in 5 ml of diethyl ether was added dropwise to 57.6 mg (2.37 mmol) of magnesium turnings in 10 ml of diethyl ether, activated by adding a few drops of dibromoethane, and the reaction mixture was heated under reflux overnight. The reaction solution was added dropwise under argon to a solution of 316 mg (2.05 mmol) of the compound from Example 73A in 10 ml of THF, and the reaction mixture was heated under reflux for 2 h. It was diluted with ethyl acetate, and the organic phase was washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 9/1) to result in 278 mg (58% of theory) of the title compound.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08063234B2
Quelldatensatzuspto-grants-2011_11
ORD IDord-1a0de785186246ae8028054f82ac8333
Quellennotizuspto-grants-2011_11