Triethylamine → 1-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Benzene, 1-bromo-3-(trifluoromethyl)-	HCID 9817	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
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	1-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene	HCID 4281885	102.2%

Reaction Conditions

Temperature	50 °C

Reaction Steps

Add copper (I) iodide (48.2 mg, 0.25 mmol), bis(triphenylphosphine)palladium (II) dichloride (155.8 m g, 0.22 mmol) and triethylamine (2.51 mL, 17.8 mmol), to a solution of 1-bromo-3-trifluoromethylbenzene (0.62 mL, 4.44 mmol) and trimethylsilylacetylene (0.81 mL, 5.78 mmol), in ethyl acetate (4 mL). Stir at 50° C. for 18h. Cool the reaction mixture to room temperature, concentrate and purify the residue by silica gel chromatography, eluting with hexanes, to give the title compound (1.1 g, 100%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915424B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-f63577125a7149d4866ada36ec1221d8
Source note	uspto-grants-2011_03