Sodium Carbonate → 3-(Pyridin-3-yl)phenol

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Bromophenol	HCID 11563	—
Reactant	3-Pyridinylboronic acid	HCID 2734378	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	3-(Pyridin-3-yl)phenol	HCID 12937948	78.8%

Reaction Conditions

Temperature	120 °C

Reaction Steps

3-Bromophenol (500 mg, 2.86 mmol) and pyridin-3-ylboronic acid (422 mg, 3.76 mmol) were dissolved in dimethoxyethane/water=5 mL/2.5 mL. Pd(dppf)Cl2 (118 mg, 0.14 mmol) and sodium carbonate (919 mg, 8.67 mmol) were added thereto, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (hexane:ethyl acetate=9:1) to obtain 3-(pyridin-3-yl)phenol (386 mg, 78%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09447083B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-dfcc3666a7d64d84adcb20b07e17bb0f
Source note	uspto-grants-2016_09