Ethyl 3-bromobenzoate → 6-Cyclopentyl-benzoic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Ethyl 3-bromobenzoate	HCID 90488	—
Reactant	HCID 178419768	HCID 178419768	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	6-Cyclopentyl-benzoic acid ethyl ester	HCID 86688277	—

Reaction Conditions

Temperature	85 °C

Reaction Steps

To 1.00 mL (6.24 mmol) ethyl 3-bromobenzoate was added 13.0 mL (6.50 mmol) 0.5 M cyclopentylzinc bromide solution in THF followed by 100 mg (0.137 mmol) 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) under argon atmosphere. The reaction mixture was stirred at 85° C. for 1.5 h, then diluted with water and stirred at RT for 12 h. The suspension was extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was filtered through Alox (EtOAC) and concentrated in vacuo.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883789B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-592a1af4737c4ee3975dbeaebcb1cea7
Source note	uspto-grants-2014_11