Triethylamine → 4,4,5,5-tetramethyl-2-{(E)-2-[4-(1-methylethyl)phenyl]ethenyl}-1,3,2-dioxaborolane

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Ethynyl-4-(1-methylethyl)benzene	HCID 637501	—
Reactant	4,4,5,5-Tetramethyl[1,3,2]dioxaborolane	HCID 2734768	—
Catalyst	Bis(cyclopenta-1,3-diene);hydride;zirconium(2+);chloride	HCID 131718033	—
Solvent	Hexane	HCID 8058	—
Product	4,4,5,5-tetramethyl-2-{(E)-2-[4-(1-methylethyl)phenyl]ethenyl}-1,3,2-dioxaborolane	HCID 68280923	91.3%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of triethylamine (246 mg), 1-ethynyl-4-isopropylbenzene (3500 mg), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3417 mg) and zirconocene chloride hydride (626 mg) was stirred at 80° C. overnight. To the reaction mixture was added hexane, and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6030 mg) as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09150591B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-346c206c78814d9c9ea001db58c115af
Source note	uspto-grants-2015_10