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

HRID 628530Notes

Reaction equation

HRID 628530 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]([CH3:19])[N:11]=2)=[C:5]([CH3:20])[CH:4]=1.Br>C(O)(=O)C>[CH3:9][C:8]1[CH:7]=[C:6]([C:10]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]([CH3:19])[N:11]=2)[C:5]([CH3:20])=[CH:4][C:3]=1[OH:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 1182364733-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

Product 1

HCID 1369702222,5-dimethyl-4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-phenolYield 101.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole (described in Reference Preparation example 85) 3 g, 47% hydrobromic acid 29 ml and acetic acid 29 ml was stirred with heating under reflux for twenty one hours. The solvent was distilled off and to the resulting residues was added ice water 90 ml. The precipitates were filtered and were washed with ice water 90 ml and hexane 100 ml, and then were concentrated under reduced pressure to give 2,5-dimethyl-4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-phenol 2.9 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for twenty one hours
  3. distillationThe solvent was distilled off and to the resulting residues
  4. additionwas added ice water 90 ml
  5. filtrationThe precipitates were filtered
  6. washwere washed with ice water 90 ml and hexane 100 ml
  7. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-63c5b36e29de447e939207b2d63ecc87
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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