Thioanisole → 4-[3-Chloro-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenol

HRID 351236Notes

Reaction equation

HRID 351236 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([Cl:28])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1(SC)C=CC=CC=1>>[Cl:28][C:17]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[N:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:18]=1

Participants

3

Reactant 2

HCID 7520ThioanisoleHCID 210909015-[4-(benzyloxy)phenyl]-3-chloro-1-(4-methoxyphenyl)-1H-pyrazole

Product 1

HCID 1357373744-[3-Chloro-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenolYield 21.3%

Procedure

A solution of 4-[3-chloro-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenyl benzyl ether (2.79 g) and thioanisole (3.56 g) intrifluoroacetic acid (25 ml) was stirred at ambient temperature overnight. The mixture was concentrated in vacuo. The residue was recrystallized from AcOEt (15 ml) and n-hexane (12 ml) to give 1st crop of FR282117 (1.48 g). The mother liqour was washed with H2O, saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=30%. The pure fractions were collected and concentrated in vacuo. The residual crystals were collected and washed with IPE to give 2nd crop of 4-[3-chloro-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenol(457.2 mg) white powder

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was recrystallized from AcOEt (15 ml) and n-hexane (12 ml)
  3. customto give 1st crop of FR282117 (1.48 g)
  4. washThe mother liqour was washed with H2O, saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with AcOEt/n-hexane=30%
  9. customThe pure fractions were collected
  10. concentrationconcentrated in vacuo
  11. customThe residual crystals were collected
  12. washwashed with IPE

Sources & evidence

ORD record
ord-a070a00f587e49959f29e4a8a3b456be
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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