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

HRID 2354995노트

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HRID 2354995 반응식
[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

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 2733271Sodium methanesulfinateHCID 687084713-(4-Bromo-3-fluoro-phenoxy)-5-methoxymethoxybenzoic acid methyl esterHCID 131727087brine NH4OH

생성물 1

HCID 687047143-(3-Fluoro-4-methanesulfonyl-phenoxy)-5-methoxymethoxybenzoic acid methyl ester수율 48%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fb3c77bbe7944fc1b8fa9abe353f6c0d
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754743B2

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