Phenylacetylene → 3-(Phenylethynyl)-1-benzofuran-5-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Phenylacetylene	HCID 10821	—
Reactant	3-Bromo-benzofuran-5-carbaldehyde	HCID 57469663	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	3-(Phenylethynyl)-1-benzofuran-5-carbaldehyde	HCID 57469665	56%

Reaction Conditions

Temperature	55 °C

Reaction Steps

In a dry flask 3-Bromo-1-benzofuran-5-carbaldehyde (1 g, 4.4 mmol) were dissolved in anhydrous THF (50 ml). To this was added under Argon Bis (triphenylphosphine) palladium(II) chloride (160 mg, 0.2 mmol), TEA (2.81 mL, 5 eq.), CuI (40 mg, 0.2 mmol) and Phenylacetylene (897 mg, 8.8 mmol). The reaction was heated at 55° C. for 2 days. The crude was filtered through celite and purified on silicagel using as eluent cyclohexan-ethyl acetate (7-3) affording 680 mg (yield: 56%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07846925B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-5485e938c9a24b97b4fba4b98ca3539d
Source note	uspto-grants-2010_12