8-Hydroxyquinoline → 4-Hydroxymethyl 1-(4-iodophenyl)imidazole

Participants

Role	Name	HCID	Charge
Reactant	8-Hydroxyquinoline	HCID 1923	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	p-Diiodobenzene	HCID 12208	—
Reactant	HCID 178519868	HCID 178519868	—
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	4-Hydroxymethyl 1-(4-iodophenyl)imidazole	HCID 59260106	—

Reaction Conditions

Temperature	130 °C

Reaction Steps

A mixture of 1,4-diiodobenzene 1-1 (4.00 g, 12.1 mmol), 4-(hydroxymethyl)imidazole II-1 (1.20 g, 12.2 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 (0.230 g, 1.21 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 0-5% MeOH in CH2Cl2 to give 4-hydroxymethyl 1-(4-iodophenyl)imidazole I-1 (0.810 g). MS 301.2 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07767697B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-a9e12e5cddb54e1693283940b760085a
Source note	uspto-grants-2010_08