4-Bromotoluene → Benzene, 1-methyl-4-(phenylethynyl)-

Participants

Role	Name	HCID	Charge
Reactant	4-Bromotoluene	HCID 7805	—
Reactant	Triisopropyl borate	HCID 21531	—
Reactant	Lithium phenylacetylide	HCID 3437284	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Tetrahydrofuran dimethoxyethane	HCID 22732251	—
Product	Benzene, 1-methyl-4-(phenylethynyl)-	HCID 3014187	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

General Procedure A. To a solution of lithium phenylacetylide (15.2 ml, 15.2 mmol) in DME (20 ml) under Argon at −78° C. was added triisopropoxylborane (3.5 ml, 15.2 mmol). The mixture was stirred at −78° C. for 1.5 hours. A solution of 1-bromo-4-methylbenzene (2 g, 11.7 mmol) in DME/THF (10 ml/10 ml) was degassed with dry argon, Pd(PPh3)4 (405 mg, 0.35 mmol) was added and the solution was degassed for another 5 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07728014B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-ec8adad63d0041a0969484598bc2e2fd
Source note	uspto-grants-2010_06