Ethyl Acetate → 2-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

https://huagongshe.com/reaction/2194584

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Bromoethyl methyl ether	HCID 80972	—
Reactant	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol	HCID 2734624	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 68465443	25.2%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1 g, 4.5 mmole), 1-bromo-2-methoxyethane (0.7 g, 5 mmole) and K2CO3 (1.3 g, 9 mmole) in DMF (10 mL) was heated at 85° C. for 20 hr, diluted by ethyl acetate, washed by water, dried over MgSO4, filtered, concentrated under vacuum, purified by ISCO (silica gel, elute: 10% ethyl acetate in hexane) to give liquid product (316 mg, 25% yield). MS (ESI) m/z: Calc. 278.2 (M+). Found: 279.3 (M++1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08334292B1
Source dataset	uspto-grants-2012_12
ORD ID	ord-4daaae064e594dfd8ec53aa3a35292b2
Source note	uspto-grants-2012_12