Nitrogen → 2-Ethyl-4-fluoro-1-nitrobenzene

https://huagongshe.com/reaction/419350

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Ethylboronic acid	HCID 521157	—
Reactant	2-Bromo-4-fluoro-1-nitrobenzene	HCID 2756993	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Ethyl-4-fluoro-1-nitrobenzene	HCID 21277365	24.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

2-Bromo-4-fluoro-1-nitrobenzene (21.8 g, 100 mmol), ethyl boronic acid (7.5 g, 100 mL), K2CO3 (40 g, 300 mL), dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium (II) (6 g) in dioxane (250 mL) and H2O (80 mL) was flushed with N2 and heated at 100° C. overnight. The reaction was diluted with EtOAc and H2O and filtered through Celite®. The organic layer was separated, concentrated and purification by flash chromatography provided the title compound (4.1 g, 24.2 mmol, 24%). 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (t, J=7.78, 3H), 2.92 (q, J=7.78, 2H), 7.01-7.11 (m, 2H), 7.98 (dd, J=8.53 Hz, J=5.53 Hz, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093239B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-1bcead23c36d43e8b2a566ac0018f095
Source note	uspto-grants-2012_01