Ethyl propiolate → Ethyl 3-(4-iodophenyl)propiolate

Participants

Role	Name	HCID	Charge
Reactant	Ethyl propiolate	HCID 12182	—
Reactant	p-Diiodobenzene	HCID 12208	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Triethylamine	HCID 8471	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Ethyl 3-(4-iodophenyl)propiolate	HCID 66800188	39.6%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a mixture of 1,4-diiodobenzene (1.0 g, 3.03 mmol), Pd(PPh3)2Cl2 (580 mg, 0.606 mmol) and CuI (115 mg, 0.606 mmol) in triethylamine (20 mL), ethyl propiolate (590 mg, 6.06 mmol) was added under N2. The resulting mixture was stirred at 80° C. for 16 h under N2. The reaction mixture was diluted with EtOAc (50 mL) and filtered. The filtrate was washed with water (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified on a silica gel column using 0-10% EtOAc in petroleum ether to afford the title compound (360 mg, 30%). 1H NMR (DMSO-d6, 400 MHz): δ 7.86 (d, 2H), 7.45 (d, 2H), 4.24 (q, 2H), 1.25 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09399646B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-1ebb9b6abd864606b35eaa3d3c730ed6
Source note	uspto-grants-2016_07