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

HRID 1509645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509645
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 260Hydrogen BromideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f387118786994a54bcdf93a664cf640f
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09224963B2

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