Propargyl alcohol → 3-(3-Chloro-4-methylphenyl)-2-propyne-1-ol

Participants

Role	Name	HCID	Charge
Reactant	Propargyl alcohol	HCID 7859	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Chloro-4-iodotoluene	HCID 2801329	—
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	3-(3-Chloro-4-methylphenyl)-2-propyne-1-ol	HCID 59407708	—

Reaction Steps

A mixture of 2-chloro-4-iodotoluene (5.00 g), copper(I) iodide (75.4 mg), triphenylphosphine (260 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (410 mg), propargyl alcohol (1.29 ml), diisopropylethylamine (13.8 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 25 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=100:0-80:20) to give the object product (2.80 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-7f96d7d06c0148a8b25b8748bca6e27d
Source note	uspto-grants-2012_03