Pyrazole → 1-p-Tolyl-1H-pyrazole

HRID 1751924Notes

Reaction equation

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

Participants

Reactant 2

HCID 1048Pyrazole

HCID 78054-Bromotoluene

Product 1

HCID 8097971-p-Tolyl-1H-pyrazole

Procedure

Following General Procedure A (125° C., 24 hours), 1H-pyrazole (102 mg, 1.5 mmol) is coupled with 1-bromo-4-methylbenzene (122 μL, 1.0 mmol). The crude brown oil is purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes=70/30) to provide 90 mg (57% 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=70/30)
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Sources & evidence

ORD record: ord-e838b52e468c4130b8200b8f644fde57
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162953B2

Reaction notes

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