Triethylamine → 2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-Bromo-o-toluidine	HCID 123538	—
Reactant	2-(Dicyclohexylphosphino)biphenyl	HCID 2734216	—
Reactant	HCID 178419189	HCID 178419189	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 46738005	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of 3-bromo-2-methylaniline (1.00 g) in dioxane (15 mL) was added triethylamine (3.0 mL), Pd(OAc)2 (60 mg), 2-dicyclohexylphosphinobiphenyl (377 mg) and pinacol borane (2.34 mL) and the reaction mixture was heated to 80° C. for 1 hour. The reaction mixture was then cooled, diluted with ethyl acetate, and reduced in vacuo. The residue was purified using flash chromatography to yield 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1.07 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07846929B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-dac5c37848be490d8bd9968a6b4e5366
Source note	uspto-grants-2010_12