Triethylamine → Methyl 2-(4-fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	Methyl (2-bromo-4-fluorophenyl)acetate	HCID 25178031	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Methyl 2-(4-fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetate	HCID 59457720	—

Reaction Conditions

Temperature	35 °C

Reaction Steps

A suspension of (trimethylsilyl)acetylene (0.696 g, 7.08 mmol), methyl 2-(2-bromo-4-fluorophenyl)acetate (A48) (0.500 g, 2.02 mmol), PPh3 (0.053 g, 0.202 mmol), CuI (39 mg, 0.202 mmol), Et3N (1.41 mL, 10.1 mmol) and PdCl2(PPh3)2 (0.142 g, 0.202 mmol) in THF (25 mL) was heated at 35° C. for 16 hours. The resulting mixture was adsorbed onto silica gel and purified using column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-40% EtOAc in petroleum benzine 40-60° C.) to yield the title compound A49 as a clear oil (0.212 g, 40%); LCMS-A: rt 6.830 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266864B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-445d03570856473fb14bf8cdbf5f7e32
Source note	uspto-grants-2016_02