Dimethylformamide → Methyl 2-cyano-4-fluoro-6-methylbenzoate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Methyl 4-fluoro-2-iodo-6-methylbenzoate	HCID 57949477	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Zinc	HCID 23994	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Methyl 2-cyano-4-fluoro-6-methylbenzoate	HCID 57949316	91%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A mixture of 2-iodo-4-fluoro-6-methyl-benzoic acid methyl ester (0.294 g, 1.0 mmol), PdCl2(dppf)2 (0.018 g, 0.025 mmol), zinc (0.002 g, 0.03 mmol), Zinc cyanide (0.234 g, 2 mmol) and DMF (3 mL) was stirred at 150° C. for 1 h. The reaction mixture was cooled to room temperature, dissolved in ethyl acetate (50 mL) and washed with water. Combined organic layer was dried (MgSO4), filtered and concentrated. Silica gel column chromatography using 10:1 hexane-ethyl acetate afforded 2-cyano-4-fluoro-6-methyl-benzoic acid methyl ester (0.175 g, 91%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968570B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-541d57e05e67425b8003e3c1899f7566
Source note	uspto-grants-2011_06