Ethanol → Ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	Sodium Acetate	HCID 517045	—
Reactant	HCID 118047306	HCID 118047306	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	Ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate	HCID 118046612	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

Into a 50-mL pressure tank reactor (10 atm), was placed 3-[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole (600 mg, 1.08 mmol, 1.00 equiv), ethanol (20 mL), Pd(dppf)Cl2 (158 mg, 0.22 mmol, 0.20 equiv), NaOAc (177 mg, 2.16 mmol, 2.00 equiv), CO (10 atm). The resulting solution was stirred overnight at 110° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30-1:10). This resulted in 300 mg (46%) of ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate as yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09447084B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-d5f3362be8ab4fff93f6f4f781b1ae2d
Source note	uspto-grants-2016_09