Carbon Tetrachloride → 1-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazole

HRID 968350노트

반응식

HRID 968350 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[O:14]C=CC=3)=[CH:11][C:10]([C:18]([F:21])([F:20])[F:19])=[N:9]2)=[CH:4][C:3]=1[C:22]#[N:23].C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:30].[Na+]>C(#N)C.O.[Ru](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([OH:30])=[O:14])=[CH:11][C:10]([C:18]([F:21])([F:20])[F:19])=[N:9]2)=[CH:4][C:3]=1[C:22]#[N:23]

참가 물질

7

반응물 3

HCID 5943Carbon TetrachlorideHCID 104487241-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-(2-furyl)pyrazoleHCID 23667635Sodium periodate

생성물 1

HCID 104700071-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazole수율 64.2%

시약·촉매·용매 3

HCID 61850Ruthenium trichloride촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-(2-furyl)pyrazole (4.0 g, 12.5 mmol) in acetonitrile (30 mL) was added carbon tetrachloride (30 mL), ruthenium chloride (0.4 g) and a solution of sodium periodate (11.9 g, 56.1 mmol) in water (45 mL). The reaction is stirred at room temperature overnight. The next day the reaction mixture was filtered through celite. The filtrate was concentrated and partitioned between ethyl acetate and HCl (1N). The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated to give 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxycarbonyl pyrazole (2.4 g, 64% yield) as pure compound. MS (ES−): 298 (M−H)− (40%).

후처리

  1. filtrationThe next day the reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between ethyl acetate and HCl (1N)
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ec871871778441158586cad7bdbfa9f6
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958356B2

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