Hydrogen Bromide → 4-(5-Chloro-1,4-dimethyl-1H-pyrazol-3-yl)-2-methylphenol

HRID 628545Notes

Reaction equation

HRID 628545 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[C:10]([CH3:16])[CH:9]=2)[C:3]=1[CH3:17].Br>C(O)(=O)C>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:16])[CH:9]=2)[C:3]=1[CH3:17]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 1180013285-Chloro-3-(4-methoxy-3-methylphenyl)-1,4-dimethyl-1H-pyrazole

Product 1

HCID 1369523674-(5-Chloro-1,4-dimethyl-1H-pyrazol-3-yl)-2-methylphenolYield 79.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-chloro-3-(4-methoxy-3-methyl-phenyl)-1,4-dimethyl-1H-pyrazole (described in Reference Preparation example 92) 0.4 g, 47% hydrobromic acid 3 ml and acetic acid 3 ml was stirred with heating under reflux for fifteen hours. The solvent was distilled off and to the resulting residues was added ethyl acetate 20 ml, and the resulting mixture was stirred at room temperature for one hour. The precipitates were filtered and were washed with hexane, and were concentrated under reduced pressure to give 4-(5-chloro-1,4-dimethyl-1H-pyrazol-3-yl)-2-methyl-phenol 0.3 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for fifteen hours
  3. distillationThe solvent was distilled off and to the resulting residues
  4. additionwas added ethyl acetate 20 ml
  5. stirringthe resulting mixture was stirred at room temperature for one hour
  6. filtrationThe precipitates were filtered
  7. washwere washed with hexane
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-abd920ba788e4c95a718a0decd142050
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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