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

HRID 567873

반응식

HRID 567873 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 23978Copper촉매HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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 solution was partitioned between ethyl acetate and dilute hydrochloric acid, and the organic phase was washed in water and in an aqueous 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 2H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

후처리

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

출처 및 근거

ORD 기록
ord-efbdaef15b4a47079767403f833f42af
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180659B2

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