Propargyl alcohol → 2-Propyn-1-ol, 3-(2,4-difluorophenyl)-

Participants

Role	Name	HCID	Charge
Reactant	Propargyl alcohol	HCID 7859	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2,4-Difluoro-1-iodobenzene	HCID 137519	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	2-Propyn-1-ol, 3-(2,4-difluorophenyl)-	HCID 23006401	—

Reaction Steps

A mixture of 2,4-difluoroiodobenzene (5.00 g), copper(I) iodide (79.4 mg), triphenylphosphine (273 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (432 mg), propargyl alcohol (1.35 ml), diisopropylethylamine (14.5 ml) and tetrahydrofuran (80 ml) was stirred at room temperature for 15 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20) to give the object product (1.03 g) as a brown oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08129361B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-02cbf228fe8442b4aebbe6031a87ed2c
Source note	uspto-grants-2012_03