N-bromobutanimide → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole

HRID 968347

반응식

HRID 968347 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)=[CH:4][C:3]=1[C:18]#[N:19].C1C(=O)N([Br:27])C(=O)C1.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][Br:27])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[N:9]2)=[CH:4][C:3]=1[C:18]#[N:19]

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 11229634Benzyl PeroxideHCID 222807792-Fluoro-5-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile

생성물 1

HCID 222807951-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole수율 50.1%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-methylpyrazole (4.0 g, 14.9 mmol) in CCl4 (75 mL) was added NBS (5.3 g, 29.7 mmol) and benzylperoxide (0.2 g, 1.49 mmol). The reaction was brought to reflux overnight. The next day the CCl4 was evaporated and the residue was partitioned between ethyl acetate and sodium bicarbonate (sat.). The organic phase was washed with water, brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography gave 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole (2.6 g, 50% yield) as pure compound: MS (CI): 348 (M+H)+ (100%).

후처리

  1. temperatureto reflux overnight
  2. customThe next day the CCl4 was evaporated
  3. customthe residue was partitioned between ethyl acetate and sodium bicarbonate (sat.)
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3387442c704c4c8bbc570ea93e3e834e
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958356B2

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