2,4-Dimethylaniline → Bis(2,4-dimethylphenyl)amine

Participants

Role	Name	HCID	Charge
Reactant	2,4-Dimethylaniline	HCID 7250	—
Reactant	Benzene, 1-bromo-2,4-dimethyl-	HCID 68503	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Product	Bis(2,4-dimethylphenyl)amine	HCID 21989085	84%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 2,4-dimethylaniline (6.05 g, 50 mmol), 2,4-dimethylbromobenzene (9.25 g, 50 mmol), Pd(dppf)Cl2 (0.88 g, 1.2 mmol), sodium tert-butoxide (KOBut) (9.6 g, 0.1 mmol) in toluene (120 mL) was degassed and heated at 100° C. overnight. The resulting mixture was worked up with dichloromethane/brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 9:1. After removal of solvent, a liquid was obtained (9.45 g, in 84% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09263681B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-3c75b1fb2f9f411fa806453f0af00bce
Source note	uspto-grants-2016_02