Toluene → Methyl 3,5-dicyclopropyl-4-(trifluoromethoxy)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Toluene	HCID 1140	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Potassium cyclopropyltrifluoroborate	HCID 23697338	—
Reactant	Methyl 3,5-dibromo-4-(trifluoromethoxy)benzoate	HCID 66764920	—
Catalyst	palladium(II) acetate	HCID 167845	—
Catalyst	Bis(adamantan-1-yl)(butyl)phosphane	HCID 11371790	—
Solvent	Water	HCID 962	—
Product	Methyl 3,5-dicyclopropyl-4-(trifluoromethoxy)benzoate	HCID 66764880	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To methyl 3,5-dibromo-4-(trifluoromethoxy)benzoate (500 mg, 1.32 mmol), Cs2CO3 (2586 mg, 7.94 mmol), Pd(OAc)2 (11.9 mg, 0.053 mmol), potassium cyclopropyltrifluoroborate (470 mg, 3.18 mmol) and di(1-adamantyl)-n-butylphosphine (28.5 mg, 0.079 mmol) was added toluene (12 mL) and water (1.2 mL). The reaction mixture was heated to 100° C. overnight. The reaction mixture was cooled to room temperature, diluted with water, extracted with DCM and evaporated in vacuo. The residue was purified by silica gel chromatography (0-20% EtOAc/hexanes) to yield the title compound (259 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08742110B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-7fd07df0264a410eac9a56bdedf98093
Source note	uspto-grants-2014_06