Benzoyl Peroxide → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole

HRID 376434

반응식

HRID 376434 반응식
[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([CH3:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C1C(=O)N([Br:27])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([CH2:15][Br:27])=[CH:13][C:12]([C:16]([F:18])([F:19])[F:17])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 222807792-Fluoro-5-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile

생성물 1

HCID 222807951-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole수율 48.3%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-methyl pyrazole(4.0 g, 14.87 mmol) in carbon tetrachloride(50 mL) was added NBS(2.65 g, 14.87 mmol) and benzoyl peroxide(0.36 g, 1.48 mmol). The reaction mixture was brought to reflux overnight. Solvent was removed on rotary evaporator under reduced pressure. Residue was partitioned between ethyl acetate(80 mL) and sodium bicarbonate(sat. 80 mL). Organic phase was separated and washed with water(60 mL); dried over sodium sulfate; filtered, concentrated and subjected to silica-gel flash chromatography (ethyl acetate : hexane, 1:10) to afford 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-bromomethyl pyrazole(2.5 g). CI mass spectrum m/z (rel. intensity) 348 (M+H, 100).

후처리

  1. temperatureto reflux overnight
  2. customSolvent was removed on rotary evaporator under reduced pressure
  3. customResidue was partitioned between ethyl acetate(80 mL) and sodium bicarbonate(sat. 80 mL)
  4. customOrganic phase was separated
  5. washwashed with water(60 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f241532119f44f07a7e5cef7ea3a638e
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020357

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