Dimethylformamide → 3-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	1-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzene	HCID 2756249	—
Reactant	2H-1,3-oxazol-2-id-4-one	HCID 53249566	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one	HCID 66891913	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To 2-oxazolidone (0.110 g, 1.26 mmol) in DMF (4 mL) was added sodium hydride (60% in mineral oil; 0.056 g, 1.39 mmol), and the mixture was stirred at 0° C. for 10 minutes. 2-Bromo-5-(trifluoromethyl)benzyl bromide (0.420 g, 1.26 mmol) was added, and the reaction was stirred at 0° C. for 1 hour. The mixture was diluted with EtOAc and H2O, and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08497381B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-c90e3a82c8d24d33ae84f2ad3321c5b8
Source note	uspto-grants-2013_07