Water → 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Triethylamine	HCID 8471	—
Reactant	N,N-Dimethylpropargylamine	HCID 81643	—
Reactant	2-Bromo-4-fluoro-1-nitrobenzene	HCID 2756993	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Product	3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine	HCID 67537237	68%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a flask charged with N,N-dimethylprop-2-yn-1-amine (737 mg, 945 μL, 8.86 mmol), 2-bromo-4-fluoro-1-nitrobenzene (1300 mg, 5.91 mmol), PdCl2(PPh3)2 (415 mg, 0.59 mmol), CuI (169 mg, 0.89 mmol) were added triethylamine (2.47 mL, 17.73 mmol) and DMF (10 mL) under N2 atmosphere. The reaction mixture was heated at 60° C. for 5 h, then poured into water (300 mL) and extracted with ethyl acetate (3×40 mL). The organic fractions were combined, dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (50-100% ethyl acetate/hexanes) yielded 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine (895 mg, 68% yield). LC/MS m/z 223.0 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08999976B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-8cb3644c64854052abfe30c3ce6d8124
Source note	uspto-grants-2015_04