Diisopropylamine → 2-Ethynyl-1-fluoro-4-nitrobenzene

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	2-Bromo-1-fluoro-4-nitrobenzene	HCID 69699	—
Reactant	TBAF tetrahydrofuran	HCID 11078149	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(benzonitrile)palladium chloride	HCID 498840	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-Ethynyl-1-fluoro-4-nitrobenzene	HCID 12687361	—

Reaction Steps

A mixture of bis(benzonitril)dichloropalladium(II) (53 mg, 0.14 mmol) and copper (I) iodide (26 mg, 0.14 mmol) in 6 mL dry THF was purged with argon for 3 minutes, then was added tri(tert-butyl phosphine) (69 ul, 0.28 mmol), TMS acetylene (0.77 ml, 5.5 mmol), 3-bromo-4-fluoronitrobenzene 505 mg, 2.295 mmol), and di-isopropylamine (0.77 ml, 5.5 mmol). The mixture was stirred at room temperature for 5 hours under argon. To the reaction mixture was added 7 mL 1 M TBAF/THF and the mixture was stirred at room temperature for 10 minutes. Workup and purification by column chromatography (silica, 5%-35% EtOAc/hexane) give 2-ethynyl-1-fluoro-4-nitro-benzene.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07294635B2
Source dataset	uspto-grants-2007_11
ORD ID	ord-dcda741809ff4ee49973b6b0b2411136
Source note	uspto-grants-2007_11