Potassium Carbonate → 3-(3,5-Dimethyl-1H-pyrazol-1-yl)phenol

HRID 1509645Notes

Reaction equation

HRID 1509645 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>Br.O>[CH3:15][C:11]1[CH:12]=[C:13]([CH3:14])[N:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[N:10]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 392404991-(3-Methoxyphenyl)-3,5-dimethyl-1H-pyrazole

Product 1

HCID 545258513-(3,5-Dimethyl-1H-pyrazol-1-yl)phenolYield 96%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 1-(3-methoxyphenyl)-3,5-dimethyl-1H-pyrazole 1 (7.10 g, 35.11 mmol) in hydrogen bromide acid (45 mL, 48%) refluxed (110-120° C.) for 19 hours under a nitrogen atmosphere. Then the mixture was cooled to ambient temperature and neutralized with a solution of K2CO3 in water until there was no gas to generate. Then the precipitate was filtered off and washed with water several times. The collected solid was dried in air under reduced pressure to afford the product as a brown solid (6.33 g in 96% yield). 1H NMR (DMSO-d6, 400 MHz): δ 2.16 (s, 3H), 2.28 (s, 3H), 6.04 (s, 1H), 6.75-6.77 (m, 1H), 6.86-6.89 (m, 2H), 7.26 (t, J=8.0 Hz, 1H), 9.73 (s, 1H). 13C NMR (DMSO-d6, 100 MHz): δ 12.29, 13.30, 107.07, 111.10, 113.94, 114.43, 129.71, 138.95, 140.70, 147.57, 157.84.

Workup

  1. filtrationThen the precipitate was filtered off
  2. washwashed with water several times
  3. customThe collected solid was dried in air under reduced pressure

Sources & evidence

ORD record
ord-f387118786994a54bcdf93a664cf640f
Source dataset
uspto-grants-2015_12
Patent number
US09224963B2

Reaction notes

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