Toluene → 4-(2-Nitrophenyl)indan-1-one

Participants

Role	Name	HCID	Charge
Reactant	Toluene	HCID 1140	—
Reactant	1-Chloro-2-nitrobenzene	HCID 6945	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-one	HCID 22032088	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-(2-Nitrophenyl)indan-1-one	HCID 58544904	91.1%

Reaction Steps

Degassed toluene (0.5 L), borolan 88 (10 g, 39 mmol), 2-chloro-1-nitrobenzene (6.3 g, 40 mmol), Pd(PPh3)4 (3 g, 2.6 mmol) and 2M Na2CO3 (200 mL) were mixed under a rapid flow of argon, and the resulting mixture was refluxed overnight. Water (200 mL) and EtOAc (500 mL) were added. The aqueous layer was separated and extracted with EtOAc (2×500 mL), and the combined extracts dried over Na2SO4. The solvent was evaporated at reduced pressure and the crude product purified by column chromatography (20% EtOAc in hexanes) to give 9 g (91%) of the biphenyl intermediate 89 as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765738B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-37b21ccea4d740cb8026f63697545f83
Source note	uspto-grants-2014_07