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

HRID 968347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968347
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 222807951-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazoleAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3387442c704c4c8bbc570ea93e3e834e
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958356B2

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