Ethyl Bromide → N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Bromide	HCID 6332	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 2734620	—
Product	N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 44629855	—

Reaction Steps

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (100 mg, 0.45 mmol) and bromoethane (200 mg, 1.8 mmol), NaH (100 mg, 1.8 mmol) in THF was stirred at room temperature overnight, and concentrated in vacuo to give the crude title compound used for the next step. MS (m/z): 276 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434726B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-d87bad50eb66433bb162f6a1119d5ebd
Source note	uspto-grants-2016_09