Pyrazole → 1-(3-Methoxyphenyl)-1H-pyrazole

HRID 1751927Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1>>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 1048Pyrazole

HCID 169713-Bromoanisole

Product 1

HCID 248884661-(3-Methoxyphenyl)-1H-pyrazole

Procedure

Following General Procedure A (125° C., 24 hours), 1H-pyrazole (102 mg, 1.5 mmol) is coupled with 1-bromo-3-methoxybenzene (126 μL, 1.0 mmol). The crude brown oil is purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes=40/60) to provide 150 mg (86% isolated yield) of the desired product as an uncolored oil.

Workup

customThe crude brown oil is purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes=40/60)
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Sources & evidence

ORD record: ord-0f2e08a0d01042a9b3e99227eaeb2c60
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162953B2

Reaction notes

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