Triethylamine → 2-Ethyl-1-fluoro-4-[2-(trimethylsilyl)ethynyl]benzene

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	Lithium Chloride	HCID 433294	—
Reactant	4-Bromo-2-ethyl-1-fluorobenzene	HCID 22641025	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-Ethyl-1-fluoro-4-[2-(trimethylsilyl)ethynyl]benzene	HCID 22641049	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a stirred solution of 4-bromo-2-ethyl-1-fluoro-benzene (2.4 g, 11.82 mmol) in N,N-dimethylformamide (100 mL), trimethylsilyl acetylene (2.0 mL, 14.19 mmol), PdCl2(PPh3)2 (500 mg, 0.72 mmol), LiCl (1 g, 23.64 mmol), CuI (25 mg, 0.1 mmol) and triethylamine (3 mL) were added and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was poured into water and extracted with diethyl ether. The extract was dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel (hexanes) to give a brown oil. 1.58 g, 61%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06818663B2
Source dataset	uspto-grants-2004_11
ORD ID	ord-3abf9204343a4dd98c599d4fb9400c59
Source note	uspto-grants-2004_11