Dichloromethane → 2-(1-Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Triethylamine	HCID 8471	—
Reactant	4,4,5,5-Tetramethyl[1,3,2]dioxaborolane	HCID 2734768	—
Reactant	Benzo[b]furan-3-yl trifluoromethanesulfonate	HCID 21480510	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-(1-Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 43811031	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a solution of trifluoromethanesulfonic acid benzofuran-3-yl ester (half of the amount from step A) in THF is added triethylamine (732 mg, 7.23 mmol), 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.2 mL of a 1.0M in THF, 3.2 mmol) and Pd(dppf)Cl2.CH2Cl2 (76 mg, 0.096 mmol). The mixture is heated at 150° C. under microwave conditions for 3 min. The mixture is filtered and the filtrate evaporated under reduced pressure. The residual oil is purified by flash chromatography using hexane/EtOAc (9:1) as eluent to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08084448B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-bff221ed776d4387965f10b2f1c3c138
Source note	uspto-grants-2011_12