Hydrogen Bromide → 2-methyl-4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-phenol

HRID 628524Notes

Reaction equation

HRID 628524 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]([CH3:18])[N:10]=2)=[CH:5][C:4]=1[CH3:19].Br>C(O)(=O)C>[CH3:19][C:4]1[CH:5]=[C:6]([C:9]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]([CH3:18])[N:10]=2)[CH:7]=[CH:8][C:3]=1[OH:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 1180013303-(4-methoxy-3-methyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

Product 1

HCID 1369523832-methyl-4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-phenolYield 527.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(4-methoxy-3-methyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole (described in Reference Preparation example 78) 0.4 g, 47% hydrobromic acid 24 ml and acetic acid 24 ml was stirred with heating under reflux for twelve hours. The solvent was distilled off and to the resulting residues was added ice water 70 ml. The precipitates were filtered and were washed with ice water 70 ml, and then were concentrated under, reduced pressure to give 2-methyl-4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-phenol 2 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for twelve hours
  3. distillationThe solvent was distilled off and to the resulting residues
  4. additionwas added ice water 70 ml
  5. filtrationThe precipitates were filtered
  6. washwere washed with ice water 70 ml
  7. concentrationwere concentrated under, reduced pressure

Sources & evidence

ORD record
ord-943843e8bed74e22898b40d66c629d55
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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