Hydrochloric Acid → [3-Chloro-5-(2-formyl-4-nitro-phenoxy)-phenyl]acetic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Fluoro-5-nitrobenzaldehyde	HCID 2734770	—
Reactant	Methyl (3-chloro-5-hydroxyphenyl)acetate	HCID 58372721	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	[3-Chloro-5-(2-formyl-4-nitro-phenoxy)-phenyl]acetic acid methyl ester	HCID 58372717	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

(3-Chloro-5-hydroxy-phenyl)-acetic acid methyl ester (2.9 g, 14.5 mmol), 2-fluoro-5-nitrobenzaldehyde (2.7 g, 15.9 mmol), and potassium carbonate (4.0 g, 28.9 mmol) were combined in 1,4-dioxane (20 mL) and stirred at 100° C. overnight. Once no starting material was seen by analytical LCMS and tlc, the mixture was worked up with EtOAc and 10% aqueous HCl, and the crude material was purified by silica gel chromatography to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08247602B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-f840ff50836c4eb3a5e1ca699de48bf0
Source note	uspto-grants-2012_08