Hexane → 1-[1-(4-cyanophenyl)4-(4-fluorophenyl)butyl]-1H-imidazole

https://huagongshe.com/reaction/1941287

Participants

Role	Name	HCID	Charge
Reactant	Hexane	HCID 8058	—
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	4-(Imidazol-1-ylmethyl)benzonitrile	HCID 1236449	—
Reactant	1-(3-Bromopropyl)-4-fluorobenzene	HCID 14737133	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	1-[1-(4-cyanophenyl)4-(4-fluorophenyl)butyl]-1H-imidazole	HCID 9905115	—

Reaction Conditions

Temperature	-70 °C

Reaction Steps

1-(4-cyanobenzyl)-imidazole (1 g, 0.0054 mol) is dissolved into dry tetrahydrofuran (30 ml) and cooled to -70° C. n-BuLi in hexane (0.0054 mol) is added dropwise into the reaction mixture. After stirring for additional 30 min at -70° C. 3-(4-fluorophenyl)propyl bromide (1.5 g, 0,0069 mol) in THF (10 ml) is added to the mixture and stirring is continued for 2 hours. Then the mixture is allowed to warm to room temperature. Saturated aqueous ammonium chloride solution is added to the mixture, shaked and then the layers are separated. THF-phase is dried and evaporated to dryness. The residue is crystallized from isopropanol as hydrogen chloride salt. The filtrate is purified by flash chromatography.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05703109
Source dataset	uspto-grants-1997_12
ORD ID	ord-b23679e879fb45dba8749288c679f6cd
Source note	uspto-grants-1997_12