Ethanol → 5-Bromo-2,4-bis(2,4-difluorophenoxy)aniline

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	Water	HCID 962	—
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	4,4'-(4-Bromo-6-nitro-1,3-phenylene)bis(oxy)bis(1,3-difluorobenzene)	HCID 90416730	—
Catalyst	Iron	HCID 23925	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	5-Bromo-2,4-bis(2,4-difluorophenoxy)aniline	HCID 90417780	96.4%

Reaction Conditions

Temperature	90 °C

Reaction Steps

The product from Example 13A (0.578 g, 1.26 mmol), iron (0.352 g, 6.31 mmol), and ammonium chloride (0.101 g, 1.89 mmol) were combined in a mixture of tetrahydrofuran (9 mL), ethanol (9 mL), water (3 mL) and heated at 90° C. for 2 hours. The mixture was cooled, filtered through Celite and the Celite pad was washed repeatedly with methanol. The filtrate was concentrated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated to afford the title compound (0.52 g, 96%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09321764B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-c71d956e61b649e890567f96dac1b692
Source note	uspto-grants-2016_04