5-[2-(benzyloxy)-5-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrazole → 2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethoxy)phenol

HRID 1692309Notes

Reaction equation

HRID 1692309 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[C:20]1[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:25][N:24]1[C:20]([C:10]2[CH:11]=[C:12]([O:15][C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:14][C:9]=2[OH:8])=[CH:21][CH:22]=[N:23]1

Participants

4

Reactant 1

HCID 594365685-[2-(benzyloxy)-5-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrazole

Product 1

HCID 1360636262-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethoxy)phenolYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-[2-(benzyloxy)-5-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrazole (Preparation 534, 2.3 g, 6.6 mmol) in methanol (25 mL) was degassed with argon before the addition of palladium on carbon (10%, 230 mg). Reaction mixture was stirred at room temperature under hydrogen atmosphere (using a balloon) for 16 hours. After filtration through Celite™, filtrate was concentrated in vacuo to afford the title compound as a white solid, 1.6 g, 94% yield.

Workup

  1. customReaction mixture
  2. customfor 16 hours
  3. filtrationAfter filtration through Celite™, filtrate
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-fc0ee32f0e4f413e8dccf1e5b3856fd7
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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