1-Ethoxy-4-ethynylbenzene → Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)ethyl-carbamate

Participants

Role	Name	HCID	Charge
Reactant	1-Ethoxy-4-ethynylbenzene	HCID 2775124	—
Reactant	tert-butyl N-(1-(4-bromophenyl)ethyl)carbamate	HCID 11983730	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Acetonitrile	HCID 6342	—
Product	Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)ethyl-carbamate	HCID 66610473	—

Reaction Conditions

Temperature	65 °C

Reaction Steps

24.6 g (168 mmol) 1-ethoxy-4-ethynyl-benzene, 52.8 g (176 mmol) [1-(4-Bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (50.2) and 42.6 mL (307 mmol) TEA are added to 400 mL ACN. The mixture is warmed to 65° C. 8.84 g (7.65 mmol) Pd(PPh3)4 and 2.91 g (15.3 mmol) CuI are added and the reaction mixture is stirred at reflux for 2 h. The mixture is cooled to r.t. and the solvent is removed in vacuo. The crude product is purified by column chromatography (hexane/EtOAC 9:1→3:1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08835472B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-c35eeda1cd3e47fda628a35dcc1b3630
Source note	uspto-grants-2014_09