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HRID 547954作成日:2026年10月25日

Boron trifluoride etherate → 2-Methyl-1-[(2-methyl-2-propanyl)oxy]-3-nitrobenzene

https://huagongshe.com/reaction/547954

反応式

関与物質

役割名称HCID仕込み量
反応物Boron trifluoride etherateHCID 8000—
反応物2-Methyl-3-nitrophenolHCID 79579—
反応物Sodium BicarbonateHCID 516892—
反応物Tert-butyl 2,2,2-trichloroethanimidateHCID 2734700—
溶媒TetrahydrofuranHCID 8028—
溶媒CyclohexaneHCID 8078—
生成物2-Methyl-1-[(2-methyl-2-propanyl)oxy]-3-nitrobenzeneHCID 45097160—

反応手順

To a solution of 2-methyl-3-nitrophenol K1 (1.1 g; 7.18 mmol) in THF (13 mL) was added cyclohexane (27 mL; a solution was maintained). tert-Butyl trichloroacetimidate K2 (5.36 mL; 28.73 mmol) was added followed by a catalytic amount of boron trifluoride etherate (143.8 μL; 1.14 mmol) and the reaction was stirred at room temperature for 15 h. The reaction was incomplete (by analytical HPLC) and an additional amount of tert-butyl trichloroacetimidate (1.4 mL; 7.51 mmol) was added (reaction remains in solution). The reaction was complete after stirring at room temperature for 5 h. Solid sodium bicarbonate was added, and the mixture was filtered, rinsed with dichloromethane and evaporated to dryness to provide a white solid. The solid was triturated with dichloromethane, the white solid filtered and discarded (=trichloroacetimide). The filtrate was concentrated and loaded onto a flash column for purification (hexane:EtOAc 9:1) to provide the pure 2-methyl-3-tert-butoxynitrobenzene K3 (1.17 g; 78%). Homogeneity by HPLC (TFA) @ 220 nm: 96%

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US07939667B2
出典データセットuspto-grants-2011_05
ORD IDord-d5561b44fd274d4aa2b41fb3a2c0fba5
出典メモuspto-grants-2011_05