Potassium Hydroxide → HCID 68692120, compound

HRID 645960Notes

Reaction equation

HRID 645960 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[N:4]([C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[N:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[CH2:27][C:28]#[N:29].[OH-].[K+]>C(O)C>[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[C:27](=[CH:15][C:14]1[CH:17]=[CH:18][C:11]([N:4]2[C:5]([C:7]([F:10])([F:9])[F:8])=[CH:6][C:2]([CH3:1])=[N:3]2)=[CH:12][CH:13]=1)[C:28]#[N:29]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 592780(2,5-Difluorophenyl)acetonitrileHCID 18449041HCID 18449041, compound

Product 1

HCID 68692120HCID 68692120, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 4-(3-methyl-5-trifluoromethyl-pyrazol-1-yl)-benzaldehyde (127 mg, 0.50 mmol) and 2,5-difluoro-phenylacetonitrile (77 mg, 0.50 mmol) in ethanol (4 mL) was added 0.5 mL of aqueous 6N KOH at room temperature. The mixture was stirred for 2 hours and the resulting precipitate was collected by filtration to give 2-(2,5-difluoro-phenyl)-3-[4-(3-methyl-5-trifluoromethyl-pyrazol-1-yl)-phenyl]-acrylonitrile (170 mg, 87% yield) as a white solid: 1H-NMR (CDCl3) δ 2.45 (s, 3H), 6.51 (s, 1H), 7.1 (m, 2H), 7.3 (m, 1H), 7.6 (d, 2H, J=9), 7.67 (s, 1H), 8.0 (d, 2H, J=9) ppm. ESMS calculated for C20H12F5N3: 389.1; Found: 390.0 (M+H)+.

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-9621c7e59b6943b393267f9a67b8ad67
Source dataset
uspto-grants-2010_04
Patent number
US07705029B2

Reaction notes

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