Cesium carbonate → 1-Benzyl-2-fluoro-3-nitro-benzene

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Potassium benzyltrifluoroboranuide	HCID 23692459	—
Reactant	1-Bromo-2-fluoro-3-nitrobenzene	HCID 40427446	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	1-Benzyl-2-fluoro-3-nitro-benzene	HCID 90037814	62.5%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a mixture 1-bromo-2-fluoro-3-nitrobenzene (800 mg, 3.6 mmol), potassium benzyltrifluoroborate (2.2 g, 10.9 mmol) and Cs2CO3 (3.6 g, 10.9 mmol) in dioxane/H2O (10:1, 18 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (60 mg, 2 mol %) and the mixture was heated to 100° C. for 8 h. The mixture was cooled to RT, diluted with H2O and extracted with EtOAc. The combined extracts were washed with H2O, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (520 mg, 62%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09394263B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-b4797b8e6f7846b4b0072baf70901add
Source note	uspto-grants-2016_07