Cesium carbonate → 1-(Dimethyl-phosphinoyl)-4-nitro-benzene

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Iodo-4-nitrobenzene	HCID 12495	—
Reactant	methylphosphonoylmethane	HCID 178503022	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(Dimethyl-phosphinoyl)-4-nitro-benzene	HCID 21897912	36.3%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A degassed suspension of 1-iodo-4-nitrobenzene (90 mg, 0.36 mmol), dimethylphosphane oxide (29.2 mg, 0.38 mmol), bis(dibenzylideneacetone)palladium (3.31 mg, 0.0036 mmol), XantPhos (6.27 mg, 0.0108 mmol), and Cs2CO3 (165 mg, 0.506 mmol) in dry dioxane (0.4 mL) was heated in a sealed tube at 90° C. for 4 h. The cooled mixture was filtered, the filtrate concentrated in vacuo, and the residue chromatographed over silica gel eluting with 5% MeOH in dichloromethane to afford 26 mg of dimethyl(4-nitrophenyl)phosphane oxide (yield: 36%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09096624B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-888e2891d838492ab0fee53c43e5e966
Source note	uspto-grants-2015_08