Methanol → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzoic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Sodium Acetate	HCID 517045	—
Reactant	5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole	HCID 86691048	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzoic acid methyl ester	HCID 86691049	99%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole (10.60 g), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (1.645 mg), sodium acetate (2.748 g) and methanol (100 mL) was placed in an autoclave and purged with CO gas. The pressure was adjusted to 5 bar and the mixture was heated at 80° C. for 16 h. After cooling the pressure was released and the solvents were distilled off in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (10.00 g, 99%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08653000B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-ab9073be8b0342ada2cc56e59ecdc24e
Source note	uspto-grants-2014_02