Dichloromethane → 1-Isopropenyl-4-(2,2,2-trifluoro-1,1-dimethylethyl)benzene

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Potassium (prop-1-en-2-yl)trifluoroborate	HCID 23670158	—
Reactant	4-(2,2,2-Trifluoro-1,1-dimethylethyl)Phenyl trifluoromethanesulfonate	HCID 86639046	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1-Propanol	HCID 1031	—
Product	1-Isopropenyl-4-(2,2,2-trifluoro-1,1-dimethylethyl)benzene	HCID 67047424	70%

Reaction Steps

The procedure described in Example 10B was followed using a mixture of 4-(2,2,2-trifluoro-1,1-dimethylethyl)phenyl trifluoromethanesulfonate (13.3 g, 40 mmol), potassium isopropenyltrifluoroborate (7.0 g, 47.6 mmol), PdCl2(dppf).CH2Cl2 (1.6 g, 1.98 mmol) and triethylamine (5.5 ml, 40 mmol) in n-propanol (400 ml). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and EtOAc (100/1) to afford 6.32 g (70% yield) of the title compound as a colorless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07622589B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-8564246158a94c56b183f4d26c8a679d
Source note	uspto-grants-2009_11