3,5-Dimethoxyphenol → 2-(3,5-Dimethoxyphenoxy)-6-fluorophenyl acetic acid

HRID 3687

反応式

HRID 3687 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([OH:12])=[O:11].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([OH:23])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.[Cu].CN(C)C=O>[CH3:22][O:21][C:19]1[CH:18]=[C:17]([CH:16]=[C:15]([O:14][CH3:13])[CH:20]=1)[O:23][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([OH:12])=[O:11]

参加物

7

反応物 3

HCID 103833,5-DimethoxyphenolHCID 11430Potassium CarbonateHCID 1234642-Chloro-6-fluorophenylacetic acid

生成物 1

HCID 543693422-(3,5-Dimethoxyphenoxy)-6-fluorophenyl acetic acid収率 86.1%

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

N,N-Dimethylformamide (20 ml) was added to 2-chloro-6-fluorophenyl acetic acid (3.77 g), 3,5-dimethoxyphenol (3.08 g), potassium carbonate (5.52 g), copper iodide (950 mg) and copper (250 mg), for stirring at 120° C. for 20 hours. The resulting reaction solution was partitioned with ethyl acetate and dilute hydrochloric acid, and the organic phase was washed in water and in a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, to distill off the solvents under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3), to recover 2-(3,5-dimethoxyphenoxy)-6-fluorophenyl acetic acid (5.27 g; yield of 86%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

後処理

  1. customThe resulting reaction solution
  2. customwas partitioned with ethyl acetate and dilute hydrochloric acid
  3. washthe organic phase was washed in water and in a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationto distill off the solvents under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3)

出典と根拠

ORDレコード
ord-83441b5019214471922280f5515c2e22
出典データセット
uspto-grants-1998_03
特許番号
US05734067

関連ノート

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