8-Hydroxyquinoline → 1-(4-iodophenyl)-4-methyl-1H-pyrazole

Participants

Role	Name	HCID	Charge
Reactant	8-Hydroxyquinoline	HCID 1923	—
Reactant	4-Methylpyrazole	HCID 3406	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	p-Diiodobenzene	HCID 12208	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	1-(4-iodophenyl)-4-methyl-1H-pyrazole	HCID 68509607	49.5%

Reaction Conditions

Temperature	130 °C

Reaction Steps

A mixture of 1,4-diiodobenzene (4.00 g, 12.1 mmol), 4-methylpyrazole (0.972 g, 12.1 mmol), 8-hydroxyquinoline (0.176 g, 1.21 mmol) and K2CO3 (1.69 g, 12.2 mmol) in DMSO (12 mL) was degassed before being charged with CuI (0.310 g, 1.63 mmol). The mixture in a sealed tube was heated at 130° C. overnight. Water and EtOAc were added. The mixture was filtered. The organic layer was separated, then applied to a silica gel column, which was eluted with hexane, then with 5% EtOAc in hexane to give 1-(4-iodophenyl)-4-methyl-1H-pyrazole (1.70 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07696352B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-3583dbfa09cc496395df0f227986dbbf
Source note	uspto-grants-2010_04