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

HRID 2354995ノート

反応式

HRID 2354995 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fb3c77bbe7944fc1b8fa9abe353f6c0d
出典データセット
uspto-grants-2010_07
特許番号
US07754743B2

反応ノート

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