4-Bromo-2-methylaniline → 4-(Dimethylphosphoryl)-2-methylaniline

Participants

Role	Name	HCID	Charge
Reactant	4-Bromo-2-methylaniline	HCID 11423	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	methylphosphonoylmethane	HCID 178503022	—
Catalyst	palladium(II) acetate	HCID 167845	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(Dimethylphosphoryl)-2-methylaniline	HCID 67052683	85.4%

Reaction Steps

To a solution of 4-bromo-2-methylaniline (0.372 g, 2.00 mmol) in 8 mL DMF was added dimethylphosphine oxide (0.171 g, 2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and potassium phosphate (0.467 g, 2.20 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150° C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-20% 7N ammonia in methanol:dichloromethane) to afford the desired product (0.313 g, 85% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09273077B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-8b750d2330fb4ac3a5b1dcbbe8a934d3
Source note	uspto-grants-2016_03