Propargyl alcohol → 3-(2-Fluorophenyl)prop-2-yn-1-ol

Participants

Role	Name	HCID	Charge
Reactant	Propargyl alcohol	HCID 7859	—
Reactant	1-Fluoro-2-iodobenzene	HCID 67673	—
Catalyst	Triphenylphosphine	HCID 11776	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Triethylamine	HCID 8471	—
Product	3-(2-Fluorophenyl)prop-2-yn-1-ol	HCID 2782696	87%

Reaction Steps

To a solution of 2-fluoro-iodobenzene (267 g, 1.2 mol) in Et3N (6L) was added propargyl alcohol (140 g, 2.5 mol, 2 equiv), followed by PdCl2(dppf) (6.1 g, 8.8 mmol, 0.007 equiv), Ph3P (12.5 g, 47.6 mmol, 0.038 equiv) and copper(I) iodide (12.6 g, 66.3 mmol, 0.053 equiv). The resulting mixture was heated at the reflux temperature for 17 h, allowed to cool to room temperature and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure and purified by vacuum distillation to give 3-(2-fluorophenyl)prop-2-yn-1-ol (156.6 g, 87%) as a deep brown oil: bp 84° C./0.3 mmHg; TLC (CH2Cl2) Rf 0.44; 1H NMR (CDCl3) δ 2.46 (d, J=5.0 Hz, 1H), 4.45 (d, J=5.0 Hz, 1H), 6.94-7.02 (m, 2H), 7.17-7.23 (m, 1H), 7.31-7.37 (m, 1H); GCMS m/z (rel abundance) 151 (MH+, 75%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06784167B2
Source dataset	uspto-grants-2004_08
ORD ID	ord-0e26c05cfb2046568b618137b75d6628
Source note	uspto-grants-2004_08