Dichloromethane → 2-chloro-N,N-diethyl-4-methylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromo-2-chloro-N,N-diethylbenzamide	HCID 16115931	—
Reactant	HCID 178477796	HCID 178477796	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-chloro-N,N-diethyl-4-methylbenzamide	HCID 885847	90%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 4-bromo-2-chloro-N,N-diethylbenzamide from Example 23, Part A (3.10 g, 10.67 mmol) in 50 mL of DMF was added potassium carbonate (3.68 g, 26.7 mmol) and dimethyl zinc (8.0 mL of a 2.0 M solution in toluene, 16.0 mmol). The solution was degassed with a stream of argon and then there was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (175 mg, 0.21 mmol). The reaction mixture was allowed to stir at 90° C. for 18 h. The reaction mixture was allowed to cool and was diluted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concentrated. The residue was purified (ISCO, elution with 0-50% EtOAc/hexane, 30 min) to afford 2.15 g (90%) of the title compound as a colorless oil. LRMS (ESI): 226.2/228.2 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07572805B2
Source dataset	uspto-grants-2009_08
ORD ID	ord-d7f44d05a3ba4aabbc7bcc6dd27c6bd4
Source note	uspto-grants-2009_08