Dimethylformamide → Tert-butyl 3-chloro-2,4-difluorobenzoate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine	HCID 547712	—
Reactant	3-Chloro-2,4-difluorobenzoic acid	HCID 2773532	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	Tert-butyl 3-chloro-2,4-difluorobenzoate	HCID 58046346	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A 125 mL, single-neck, round-bottomed flask was charged with di-tert-butoxy-N,N-dimethylmethanamine (48.2 ml, 201 mmol), 3-chloro-2,4-difluorobenzoic acid (9.67 g, 50.2 mmol), and DMF (50 ml). The reaction was heated to 80° C. for 48 hours. After cooling to ambient temperature, the reaction was diluted with saturated NaHCO3 and EtOAc. The aqueous phase was extracted with EtOAc, and the combined organic phases were washed with saturated NaHCO3 and brine, dried, filtered and concentrated to provide the desired product as a gold oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08648087B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-fa4412622b96455780588c4a1f85a6ca
Source note	uspto-grants-2014_02