Water → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole

HRID 968348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968348
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13]Br)=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)=[CH:4][C:3]=1[C:19]#[N:20].[OH2:21]>CS(C)=O.[Cu-]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:21])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)=[CH:4][C:3]=1[C:19]#[N:20]

Komponenten

5

Edukt 2

HCID 962WaterHCID 222807951-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole

Produkt 1

HCID 222807401-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazoleAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419072HCID 178419072, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole (0.6 g, 1.72 mmol) in DMSO (10 mL) was added copper (I) oxide (0.52 g, 3.62 mmol) and water (3 mL). The reaction was stirred at 60° C. overnight. The next day the reaction mixture was filtered through celite. The filtrate was partitioned between ethyl acetate and water. The organic was washed three times with water, brine, dried over sodium sulfate, filtered and concentrated to leave 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethyl pyrazole (0.45 g, 92% yield) as pure compound: MS (CI): 286 (M+H)+ (100%).

Aufarbeitung

  1. filtrationThe next day the reaction mixture was filtered through celite
  2. customThe filtrate was partitioned between ethyl acetate and water
  3. washThe organic was washed three times with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f883405d58a64c40ae317e39e0df33fd
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958356B2

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