Dichloromethane → HCID 86677538, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Methyl 1-methoxy-4-bromo-2-naphthoate	HCID 12084039	—
Reactant	Potassium vinyltrifluoroborate	HCID 23679353	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86677538	HCID 86677538	—

Reaction Conditions

Temperature	65 °C

Reaction Steps

To a solution of methyl 4-bromo-1-methoxy-2-naphthoate (see Example 2, 5.00 g, 16.9 mmol) in a 105 mL of a 20:1 mixture of THF:water under an atmosphere of nitrogen was added potassium carbonate (2.58 g, 18.6 mmol), potassium vinyltrifluoroborate (3.40 g, 25.4 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II), 1:1 complex with dichloromethane (1.24 g, 1.69 mmol). The reaction was heated at 65° C. for 65 hours, cooled to room temperature, diluted with ethyl acetate, and filtered through celite. The filtrate was concentrated in vacuo to provide methyl 4-formyl-1-methoxy-2-naphthoate that gave a mass ion (ES+) of 242.3 for [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883850B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-260e455568064d53b2807da0478d132f
Source note	uspto-grants-2014_11