Triethylamine → ((3,4-Difluorophenyl)ethynyl)trimethylsilane

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	4-Bromo-1,2-difluorobenzene	HCID 67675	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178419050	HCID 178419050	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	((3,4-Difluorophenyl)ethynyl)trimethylsilane	HCID 67047877	100.6%

Reaction Conditions

Temperature	50 °C

Reaction Steps

Add copper (I) iodide (109.4 mg, 0.57 mmol), bis(triphenylphosphine)palladium (II) dichloride (365 mg, 0.52 mmol) and triethylamine (5.88 mL, 41.6 mmol), to a solution of 4-bromo-1,2-difluorobenzene (1.17 mL, 10.4 mmol) and trimethylsilylacetylene (1.89 mL, 13.5 mmol), in ethyl acetate (8 mL). Stir at 50° C. for 18h. Cool to room temperature, concentrate and purify the residue by silica gel chromatography, eluting with hexanes, to give the title compound (2.20 g, 100%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915424B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-a32602843c3e41318d4223dc3aee1ed5
Source note	uspto-grants-2011_03