Toluene → 1-Methoxy-4-(pentafluoroethyl)benzene

Participants

Role	Name	HCID	Charge
Reactant	Toluene	HCID 1140	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Propanoic acid, 2,2,3,3,3-pentafluoro-, potassium salt (1:1)	HCID 23667659	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Product	1-Methoxy-4-(pentafluoroethyl)benzene	HCID 12871966	—

Reaction Conditions

Temperature	140 °C

Reaction Steps

8.3 g of potassium pentafluoropropionate and 9.8 g of CuI are introduced, under an inert atmosphere, into a 500 mL three-necked flasked equipped with Dean-Stark apparatus and a condenser. 90 mL of DMF and 110 mL of toluene are added. The medium is heated to 140° C. under nitrogen, and 80 mL of toluene are distilled off. The medium is then cooled to RT and then deoxygenated by sparging with nitrogen. 6 g of iodoanisole are then added and the mixture is then heated at 155° C. for 20 hours. After cooling to RT, the medium is diluted with 200 mL of a water/ethyl ether mixture. The medium is then filtered through Celite®. The organic phase is washed 3 times with water, dried over MgSO4 and then evaporated to give 4.3 g of a brown oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07598392B2
Source dataset	uspto-grants-2009_10
ORD ID	ord-e4e89bb11fb54884ac95ad8e69af09c5
Source note	uspto-grants-2009_10