Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 90165962, compound

https://huagongshe.com/reaction/2200081

Participants

Role	Name	HCID	Charge
Reactant	Benzene, 1-bromo-4-(trifluoromethyl)-	HCID 67872	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	tert-butyl N-(morpholin-2-ylmethyl)carbamate	HCID 19081107	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	HCID 90165962	HCID 90165962	44%

Reaction Conditions

Temperature	105 °C

Reaction Steps

tert-Butyl morpholin-2-ylmethylcarbamate (1.0 g, 4.62 mmol), 1-bromo-4-(trifluoromethyl)benzene (1.04 g, 4.62 mmol), Pd(dba)2 (133 mg, 0.23 mmol), X-Phos (220 mg, 0.46 mmol) and sodium tert-butoxide (533 mg, 5.55 mol) were combined in 10 mL of dry toluene in a sealed tube. The mixture was degassed with argon and then stirred at 105° C. for 4 h. The mixture was filtered through a layer of Celite and rinsed with THF. Solvents were evaporated and the residue was extracted with water and ethyl acetate. The organic layer was dried and concentrated. The residue was purified by ISCO flash column chromatography (50 g silica gel, ethyl acetate in hexanes 0% to 80%) to give the desired compound (727 mg, 44%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09359337B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-96e48b7489904d7f833d72793f12b408
Source note	uspto-grants-2016_06