1-(2-Benzyloxyphenyl)-4-fluoro-3,5-dimethyl-1H-pyrazole → 2-(4-Fluoro-3,5-dimethyl-1H-pyrazol-1-yl)phenol

HRID 337354Notes

Reaction equation

HRID 337354 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]([CH3:20])=[C:18]([F:21])[C:17]([CH3:22])=[N:16]1)C1C=CC=CC=1>CO.[Pd]>[F:21][C:18]1[C:17]([CH3:22])=[N:16][N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[C:19]=1[CH3:20]

Participants

4

Reactant 1

HCID 867032601-(2-Benzyloxyphenyl)-4-fluoro-3,5-dimethyl-1H-pyrazole

Product 1

HCID 601440492-(4-Fluoro-3,5-dimethyl-1H-pyrazol-1-yl)phenolYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

416 mg of 1-(2-benzyloxyphenyl)-4-fluoro-3,5-dimethyl-1H-pyrazol was dissolved in 16 ml of methanol, and 42.6 mg of 10% palladium/carbon was added and stirred under hydrogen atmosphere at room temperature for a whole day and night. After the insoluble matter was filtered off, the filtrate was distilled off under reduced pressure and the resulting residue was purified using silica gel column chromatography (hexane:ethyl acetate=5:1) to yield 290 mg of the title compound.

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. distillationthe filtrate was distilled off under reduced pressure
  3. customthe resulting residue was purified

Sources & evidence

ORD record
ord-7cf7066bbafc45cbbdaccda731848d36
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

Loading…