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HRID 561452作成日:2026年10月26日

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

https://huagongshe.com/reaction/561452

反応式

関与物質

役割名称HCID仕込み量
反応物Diethyl EtherHCID 3283—
反応物2-Bromo-4-chloroanisoleHCID 521935—
反応物MagnesiumHCID 5462224—
反応物2-Cyano-N-methoxy-N-methylcyclopropanecarboxamideHCID 58392506—
触媒1,1-DibromoethaneHCID 11201—
溶媒TetrahydrofuranHCID 8028—
溶媒Ethyl AcetateHCID 8857—
生成物2-(4-Chloro-2-methoxybenzoyl)cyclopropanecarbonitrileHCID 58392548—

反応手順

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.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US08063234B2
出典データセットuspto-grants-2011_11
ORD IDord-1a0de785186246ae8028054f82ac8333
出典メモuspto-grants-2011_11