Potassium Carbonate → 5-(4-chlorophenyl)-3,4-dihydro-2H-pyran

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Chlorophenylboronic acid	HCID 74299	—
Reactant	5-bromo-3,4-dihydro-2H-pyran	HCID 5325865	—
Reactant	Water ethanol	HCID 19096565	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Product	5-(4-chlorophenyl)-3,4-dihydro-2H-pyran	HCID 86698859	58.8%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 5-bromo-3,4-dihydro-2H-pyran (1.0 g, 6.13 mmol), (4-chlorophenyl)boronic acid (1.05 g, 6.74 mmol), potassium carbonate (2.5 g, 18.4 mmol), Pd(dppf)Cl2 (449 mg, 0.613 mmol), and ethanol/water (2/2 mL) in toluene (10 mL) was stirred at 100° C. for 12 hours. The mixture was filtered, and the filtrate was evaporated and purified by silica gel chromatography to give the title compound (700 mg, 58.8%) as orange solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.25 (d, 2H), 7.20 (d, 2H) 6.90 (s, 1H), 4.03 (t, 2H), 2.37 (t, 2H), 2.02 (m, 2H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889730B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-413b92b2dc0943a2ae26205ad8f8e95b
Source note	uspto-grants-2014_11