1,1,1-Trifluoro-2,4-pentanedione → 2-Fluoro-5-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile

HRID 1063490

반응식

HRID 1063490 반응식
[Sn](Cl)(Cl)(Cl)Cl.[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][NH2:14])=[CH:9][C:8]=1[C:15]#[N:16].[F:17][C:18]([F:26])([F:25])[C:19](=O)[CH2:20][C:21](=O)[CH3:22]>C(O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21]([CH3:22])=[CH:20][C:19]([C:18]([F:26])([F:25])[F:17])=[N:14]2)=[CH:9][C:8]=1[C:15]#[N:16]

참가 물질

4

반응물 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 688056624-Fluoro-3-cyanophenylhydrazine tin chloride

생성물 1

HCID 222807792-Fluoro-5-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile수율 56%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 4-fluoro-3-cyanophenylhydrazine tin chloride (20 g, 53.6 mmol) in ethanol (150 mL) was added 1,1,1-trifluoro-2,4-pentanedione (8.18 g, 53.6 mmol). The reaction was brought to reflux overnight. The next day the ethanol was evaporated and the residue partitioned between ethyl acetate and HCl (1 N). The aqueous phase was extracted with ethyl acetate (4×20 mL). The organic phase is washed with water, brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography gave 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-methylpyrazole (8 g, 56% yield) as pure compound: MS (CI): 270 (M+H)+ (100%).

후처리

  1. temperatureto reflux overnight
  2. customThe next day the ethanol was evaporated
  3. customthe residue partitioned between ethyl acetate and HCl (1 N)
  4. extractionThe aqueous phase was extracted with ethyl acetate (4×20 mL)
  5. washThe organic phase is washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0eef331d4ce14b31b05de00e7f2e350e
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06965036B2

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