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

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Propargyl alcohol	HCID 7859	—
Edukt	Triphenylphosphine	HCID 11776	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	3-Chloro-4-iodobenzotrifluoride	HCID 2736612	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	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	—
Lösungsmittel	Tetrahydrofuran	HCID 8028	—
Lösungsmittel	Sodium chloride; water	HCID 57417360	—
Produkt	3-(2-Chloro-4-trifluoromethylphenyl)-2-propyne-1-ol	HCID 59407914	—

Reaktionsschritte

A mixture of 3-chloro-4-iodobenzotrifluoride (5.00 g), copper(I) iodide (62.1 mg), triphenylphosphine (214 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (337 mg), propargyl alcohol (1.06 ml), diisopropylethylamine (11.4 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 17 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 (3.05 g) as a brown solid.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08129361B2
Quelldatensatz	uspto-grants-2012_03
ORD ID	ord-68a34da2ecc944269a048df9e274ed49
Quellennotiz	uspto-grants-2012_03