Methanol → 2-(2,5-Bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Phenylacetylene	HCID 10821	—
Reactant	1,3,4-Oxadiazole	HCID 97428	—
Reactant	Methylenechloride Hexane	HCID 21226440	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Product	2-(2,5-Bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole	HCID 58820758	72%

Reaction Steps

Pd(PPh3)4 (71.6 mg, 0.1 mmol) and CuI (23.6 mg, 0.1 mmol) were added to a mixture of 2,(2,5-dibromophenyl)-5-[4-octyloxy)phenyl]-1,3,4-oxadiazole (3.20 g, 6.3 mmol) and phenyl acetylene (1.29 g, 12.6 mmol) in 20 mL of dry Et3N. The reaction mixture was magnetically stirred for 3 h under reflux. The cooled reaction mixture was poured into an excess amount of methanol and the precipitate was collected by filtration. Re-crystallization from methylene chloride/hexane gave 2-(2,5-bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole (2.50 g, 72% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07192657B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-340e44f6bf814d0e96218d1447b0f382
Source note	uspto-grants-2007_03