Ethyl Acetate → 3-(3-Fluoro-4-methanesulfonyl-phenoxy)-5-methoxymethoxybenzoic acid methyl ester

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Reaktionsgleichung

[CH3:1][S:2]([O-:4])=[O:3].[Na+].[CH3:6][O:7][C:8](=[O:28])[C:9]1[CH:14]=[C:13]([O:15][CH2:16][O:17][CH3:18])[CH:12]=[C:11]([O:19][C:20]2[CH:25]=[CH:24][C:23](Br)=[C:22]([F:27])[CH:21]=2)[CH:10]=1.O.[Cl-].[Na+].O.N.C(OC(=O)C)C>CS(C)=O.[Cu](I)I>[CH3:6][O:7][C:8](=[O:28])[C:9]1[CH:14]=[C:13]([O:15][CH2:16][O:17][CH3:18])[CH:12]=[C:11]([O:19][C:20]2[CH:25]=[CH:24][C:23]([S:2]([CH3:1])(=[O:4])=[O:3])=[C:22]([F:27])[CH:21]=2)[CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

After adding 757 mg (7.41 mmol) of sodium methanesulfinate and 1.41 g (7.41 mmol) of copper iodide to a solution of 357 mg (0.93 mmol) of the obtained ester compound in dimethylsulfoxide (6.0 ml), the reaction mixture was stirred at 120° C. for 6 hours. Sodium chloride water-ammonia water (9:1) was added to the reaction mixture and extraction was performed with acetic acid ethyl ester, and then the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=2:1) to obtain 170 mg of 3-(3-fluoro-4-methanesulfonyl-phenoxy)-5-methoxymethoxybenzoic acid methyl ester (yield: 48%) as a colorless oil.

Aufarbeitung

washthe organic layer was washed with brine
customdried
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=2:1)

Quellen und Nachweise

ORD-Eintrag: ord-fb3c77bbe7944fc1b8fa9abe353f6c0d
Quelldatensatz: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07754743B2

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