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

HRID 2113811Notes

Reaction equation

[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

Participants

Conditions

Temperature: 120 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-c69a3ff1e37b4a4a83b897a0d92a7c5c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432287B2

Reaction notes

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